32981-86-5

Basic information

• Product Name: 10-Deacetylbaccatin III
• Synonyms: 10-Deacetyl Baccatin lll;Docetaxel IMpurity E (10-Deacetyl Baccatin III);ó;7,11-Methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one, 12b-(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-;Docetaxel impurity E;10-Deacetylbaccatin III, >=99%;10-deacetyl Chiba Cardin Ⅲ;12b-(Acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3
• CAS NO: 32981-86-5
• Molecular Formula: C₂₉H₃₆O₁₀
• Molecular Weight: 544.59
• EINECS: 418-680-6
• Product Categories: chemical reagent;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;plant extract;Inhibitors;Miscellaneous Natural Products;Intermediates & Fine Chemicals;Pharmaceuticals;Antibiotics;Antibiotics A to;Antibiotics A-FAntibiotics;Antibiotics by Application;Antineoplastic and Immunosuppressive AntibioticsAntibiotics;Interferes with DNA Synthesis;Mechanism of Action;APIS;Pharmaceutical intermediate
• Mol File: 32981-86-5.mol
• Article Data: 27

Chemical Properties

• Melting Point: 231-236 °C
• Boiling Point: 717℃
• Flash Point: >110°(230°F)
• Appearance: white/Powder
• Density: 1.2007 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5376 (estimate)
• Storage Temp.: 2-8°C
• Solubility: methanol: soluble, clear, colorless (5 mg + 0.1 mL MeOH)
• PKA: 11.50±0.70(Predicted)
• Water Solubility: INSOLUBLE
• CAS DataBase Reference: 10-Deacetylbaccatin III(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Deacetylbaccatin III(32981-86-5)
• EPA Substance Registry System: 10-Deacetylbaccatin III(32981-86-5)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 45-38-36/37/39-28A-24/25
• RIDADR: 1544
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 32981-86-5(Hazardous Substances Data)

Usage

Chemical Properties

10-Deacetylbaccatin III is White Solid

Uses

Different sources of media describe the Uses of 32981-86-5 differently. You can refer to the following data:
1. 10-DAB (10-Deacetylbaccatin) is an antineoplastic agent and an anti-cancer intermediate. 10-DAB (10-Deacetylbaccatin) has gained great attention because of its partly excellent anti-cancer properties. 10-DAB (10-Deacetylbaccatin) can be gained from the le
2. 10-Deacetyl Baccatin III is an impurity of Paclitaxel (P132500) and derivatives.
3. 10-Deacetylbaccatin III is a intermediate in the synthesis of Taxol and derivatives

Biological Activity

10-dab (also known as 10-deacetylbaccatin) is an intermediate used for the preparation of taxol, an anti-leukemic and tumor-inhibiting agent isolated from the inner bark of the pacific yew tree taxus brevifolia as well as other species of the genus taxus. due to the low availability of taxol from its natural sources, 10-dab is used as a raw material for the preparation of taxol and its derivatives. being easily extracted from the annual cute of the yew leaves, 10-dab has a very folded chemical structure with the α hydroxyl group hindered at c-13 easily to form a hydrogen bond with the 4α acetyl group.f. gueritte-voegelein, v. senilh, b. david, d. guenard and p. potier. chemical studies of 10-deacetyl baccatin iii hemisynthesis of taxol derivatives. tetrahedron 1986; 42(16): 4451-4460

InChI:InChI=1/C29H36O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,21-22,24,31-33,36H,11-13H2,1-5H3/t17-,18+,19+,21+,22+,24-,27-,28+,29+/m0/s1

Synthetic route

7-triethylsilyl-10-deacetylbaccatin III (115437-18-8) → 10-deacetylbaccatin III (32981-86-5)

Conditions	Yield
With sodium periodate In tetrahydrofuran; water at 30 - 40℃; for 144h;	88%
With hydrogenchloride In ethanol at 0℃; for 24h;	67%
With sodium hypochlorite In acetone; acetonitrile at 20℃; for 2h;

baccatin III (27548-93-2) → 10-deacetylbaccatin III (32981-86-5)

Conditions	Yield
With hydrazine hydrate In ethanol for 2h; Ambient temperature;	87%
With dihydrogen peroxide; calcium carbonate In tetrahydrofuran for 72h; Ambient temperature;	57%

taxol (33069-62-4) → 10-deacetylbaccatin III (32981-86-5) + methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (32981-85-4) + 10-deacetyl-7-epi-baccatin III (71629-92-0)

Conditions	Yield
With lithium iodide In methanol for 10h; Ambient temperature;	A 58% B 82% C 40%
With lithium iodide In methanol for 10h; Ambient temperature;	A 58% B 82% C 40%

taxol (33069-62-4) → 10-deacetylbaccatin III (32981-86-5)

Conditions	Yield
With hydrazine hydrate In ethanol for 2h; Ambient temperature;	82%
Multi-step reaction with 2 steps 1: 81 percent / pyridine / CH2Cl2 / Ambient temperature 2: 22 percent / LiI / methanol / Ambient temperature; 2 weeks View Scheme

7-O-chloroacetylbaccatin III (500726-11-4) → 10-deacetylbaccatin III (32981-86-5)

Conditions	Yield
With water; hydrazine In ethanol at 20℃; for 2h; Product distribution / selectivity;	75%

7-O-acetylbaccatine III (32981-90-1) → 10-deacetylbaccatin III (32981-86-5)

Conditions	Yield
With water; hydrazine In ethanol at 20℃; for 2h; Product distribution / selectivity;	75%
With sodium methylate at 20℃; for 2h; Product distribution / selectivity;	75%

(2aR,4S,4aS,6R,9S,11S,12S,12bS)-6,12b-bis(acetyloxy)-9-({(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl}oxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9, 10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate (148930-54-5) → 10-deacetylbaccatin III (32981-86-5) + methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (32981-85-4) + 10-deacetyl-7-epi-baccatin III (71629-92-0)

Conditions	Yield
With lithium iodide In methanol Ambient temperature; 2 weeks;	A 22% B 71% C 34%

10-deacetyl-7-epi-baccatin III (71629-92-0) → 10-deacetylbaccatin III (32981-86-5)

Conditions	Yield
With Bacillus mycoides AS1.182 In acetone at 27℃; for 168h;	58.9%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In xylene at 80℃; Product distribution; C-7-epimerization under base conditions; further taxoids;

10-dehydro-10-deacetylbaccatin III (V) (191276-24-1) → 10-deacetylbaccatin III (32981-86-5)

Conditions	Yield
With sodium cyanoborohydride	56%

7-α-glucosyloxyacetyl paclitaxel (197013-82-4) → 10-deacetylbaccatin III (32981-86-5) + 10-deacetyl-7-epi-baccatin III (71629-92-0) + baccatin III (27548-93-2) + 7-epi-baccatine III (31077-81-3)

Conditions	Yield
With Synechocystis sp. PCC 6803; BG-11 medium at 25℃; for 168h; Further byproducts.;	A 16% B 10% C 33% D 27%

7-α-glucosyloxyacetyl paclitaxel (197013-82-4) → 10-deacetylbaccatin III (32981-86-5) + taxol (33069-62-4) + baccatin III (27548-93-2)

Conditions	Yield
With Nicotiana tabacum at 25℃;	A 10% B 25% C 11%

10-deacetylpaclitaxel (78432-77-6) → 10-deacetylbaccatin III (32981-86-5)

Conditions	Yield
In dichloromethane	24%

7-α-glucosyloxyacetyl paclitaxel (197013-82-4) → 10-deacetylbaccatin III (32981-86-5) + 10-deacetylpaclitaxel (78432-77-6) + taxol (33069-62-4) + 7-epipaclitaxel (105454-04-4)

Conditions	Yield
With Marchantia polymorpha; BG-11 medium at 25℃; Further byproducts.;	A 8% B 10% C 17% D 8%

methanol (67-56-1) + Cephalomannine (71610-00-9) → 7-epi-baccatin III (31077-81-3) + 10-deacetylbaccatin III (32981-86-5) + (2R,3S)-2-Hydroxy-3-((E)-2-methyl-but-2-enoylamino)-3-phenyl-propionic acid methyl ester (71610-01-0) + baccatin III (27548-93-2)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 5h; Ambient temperature; other base; Further byproducts given;	A 4.5 mg B 4.6 mg C 6.6 mg D 4.9 mg

Cephalomannine (71610-00-9) → 7-epi-baccatin III (31077-81-3) + 10-deacetylbaccatin III (32981-86-5) + (2R,3S)-2-Hydroxy-3-((E)-2-methyl-but-2-enoylamino)-3-phenyl-propionic acid methyl ester (71610-01-0) + baccatin III (27548-93-2)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 5h; Ambient temperature; Further byproducts given;	A 4.5 mg B 4.6 mg C 6.6 mg D 4.9 mg

Cephalomannine (71610-00-9) → 7-epi-baccatin III (31077-81-3) + 10-deacetylbaccatin III (32981-86-5) + (1Z,3E,9Z)-1-Chlorohexadeca-5,7-diyne-1,3,9-trien-14-ol (76480-33-6, 539851-34-8) + baccatin III (27548-93-2)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 5h; Ambient temperature; Further byproducts given;	A 4.5 mg B 4.6 mg C 6.6 mg D 4.9 mg

Cephalomannine (71610-00-9) → 10-deacetylbaccatin III (32981-86-5) + (2R,3S)-2-Hydroxy-3-((E)-2-methyl-but-2-enoylamino)-3-phenyl-propionic acid methyl ester (71610-01-0) + 10-Deacetylcephalomannine (76429-85-1) + baccatin III (27548-93-2)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 5h; Ambient temperature; Further byproducts given;	A 4.6 mg B 6.6 mg C 1.6 mg D 4.9 mg

Cephalomannine (71610-00-9) → 10-deacetylbaccatin III (32981-86-5) + (2R,3S)-2-Hydroxy-3-((E)-2-methyl-but-2-enoylamino)-3-phenyl-propionic acid methyl ester (71610-01-0) + 10-deacetyl-7-epi-baccatin III (71629-92-0) + baccatin III (27548-93-2)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 5h; Ambient temperature; Further byproducts given;	A 4.6 mg B 6.6 mg C 3.3 mg D 4.9 mg

phenyllithium (591-51-5) + C28H33Cl3O13 (187961-12-2) → 10-deacetylbaccatin III (32981-86-5) + baccatin III (27548-93-2)

Conditions	Yield
In tetrahydrofuran at -78℃; Phenylation;

baccatin III (27548-93-2) → 10-deacetylbaccatin III (32981-86-5) + 10-deacetyl-7-epi-baccatin III (71629-92-0)

Conditions	Yield
With zinc(II) chloride In methanol at 20℃;	A 15 mg B 46 mg

C29H48O7Si (187960-83-4) → 10-deacetylbaccatin III (32981-86-5)

Conditions

Yield

Multi-step reaction with 16 steps 1: 91 percent / tetrahydrofuran / -78 °C 2: 94 percent / HCl; H2O; NaI / dioxane 3: 92 percent / pyridine / CH2Cl2 / -30 °C 4: Dess-Martin periodinane / CH2Cl2 5: Et3N 6: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 7: N,N-diisopropylethylamine / 55 °C 8: NH4F / methanol / 20 °C 9: tetrahydrofuran / -78 °C 10: imidazole / CHCl3 11: 92 percent / pyridine / CH2Cl2 12: 76 percent / KCN / ethanol / 0 °C 13: 95 percent / (i-Pr)2NEt / toluene / 110 °C 14: 89 percent / DMAP 15: 96 percent / TASF / tetrahydrofuran / 0 °C 16: tetrahydrofuran / -78 °C View Scheme

((1S,5S,6R,7S,8S,9S,12S)-8,9-Dihydroxy-7,11,14,14-tetramethyl-3-oxo-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-en-6-yl)-acetaldehyde (187960-85-6) → 10-deacetylbaccatin III (32981-86-5)

Conditions

Yield

Multi-step reaction with 14 steps 1: 92 percent / pyridine / CH2Cl2 / -30 °C 2: Dess-Martin periodinane / CH2Cl2 3: Et3N 4: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 5: N,N-diisopropylethylamine / 55 °C 6: NH4F / methanol / 20 °C 7: tetrahydrofuran / -78 °C 8: imidazole / CHCl3 9: 92 percent / pyridine / CH2Cl2 10: 76 percent / KCN / ethanol / 0 °C 11: 95 percent / (i-Pr)2NEt / toluene / 110 °C 12: 89 percent / DMAP 13: 96 percent / TASF / tetrahydrofuran / 0 °C 14: tetrahydrofuran / -78 °C View Scheme

C31H52O7Si → 10-deacetylbaccatin III (32981-86-5)

Conditions

Yield

Multi-step reaction with 15 steps 1: 94 percent / HCl; H2O; NaI / dioxane 2: 92 percent / pyridine / CH2Cl2 / -30 °C 3: Dess-Martin periodinane / CH2Cl2 4: Et3N 5: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 6: N,N-diisopropylethylamine / 55 °C 7: NH4F / methanol / 20 °C 8: tetrahydrofuran / -78 °C 9: imidazole / CHCl3 10: 92 percent / pyridine / CH2Cl2 11: 76 percent / KCN / ethanol / 0 °C 12: 95 percent / (i-Pr)2NEt / toluene / 110 °C 13: 89 percent / DMAP 14: 96 percent / TASF / tetrahydrofuran / 0 °C 15: tetrahydrofuran / -78 °C View Scheme

((1S,5S,6R,7S,8S,12S)-7,11,14,14-Tetramethyl-3,9-dioxo-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-en-6-yl)-acetaldehyde → 10-deacetylbaccatin III (32981-86-5)

Conditions

Yield

Multi-step reaction with 12 steps 1: Et3N 2: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 3: N,N-diisopropylethylamine / 55 °C 4: NH4F / methanol / 20 °C 5: tetrahydrofuran / -78 °C 6: imidazole / CHCl3 7: 92 percent / pyridine / CH2Cl2 8: 76 percent / KCN / ethanol / 0 °C 9: 95 percent / (i-Pr)2NEt / toluene / 110 °C 10: 89 percent / DMAP 11: 96 percent / TASF / tetrahydrofuran / 0 °C 12: tetrahydrofuran / -78 °C View Scheme

((1S,5S,6R,7S,8S,9S,12S)-9-Hydroxy-7,11,14,14-tetramethyl-3-oxo-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-en-6-yl)-acetaldehyde (187961-05-3) → 10-deacetylbaccatin III (32981-86-5)

Conditions

Yield

Multi-step reaction with 13 steps 1: Dess-Martin periodinane / CH2Cl2 2: Et3N 3: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 4: N,N-diisopropylethylamine / 55 °C 5: NH4F / methanol / 20 °C 6: tetrahydrofuran / -78 °C 7: imidazole / CHCl3 8: 92 percent / pyridine / CH2Cl2 9: 76 percent / KCN / ethanol / 0 °C 10: 95 percent / (i-Pr)2NEt / toluene / 110 °C 11: 89 percent / DMAP 12: 96 percent / TASF / tetrahydrofuran / 0 °C 13: tetrahydrofuran / -78 °C View Scheme

2-((1S,5S,6S,7S,8S,12S)-7,11,14,14-Tetramethyl-3,9-dioxo-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-en-6-yl)-propenal (187960-87-8) → 10-deacetylbaccatin III (32981-86-5)

Conditions

Yield

Multi-step reaction with 11 steps 1: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 2: N,N-diisopropylethylamine / 55 °C 3: NH4F / methanol / 20 °C 4: tetrahydrofuran / -78 °C 5: imidazole / CHCl3 6: 92 percent / pyridine / CH2Cl2 7: 76 percent / KCN / ethanol / 0 °C 8: 95 percent / (i-Pr)2NEt / toluene / 110 °C 9: 89 percent / DMAP 10: 96 percent / TASF / tetrahydrofuran / 0 °C 11: tetrahydrofuran / -78 °C View Scheme

(1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-ene-3,9-dione (187961-09-7) → 10-deacetylbaccatin III (32981-86-5)

Conditions	Yield
Multi-step reaction with 8 steps 1: tetrahydrofuran / -78 °C 2: imidazole / CHCl3 3: 92 percent / pyridine / CH2Cl2 4: 76 percent / KCN / ethanol / 0 °C 5: 95 percent / (i-Pr)2NEt / toluene / 110 °C 6: 89 percent / DMAP 7: 96 percent / TASF / tetrahydrofuran / 0 °C 8: tetrahydrofuran / -78 °C View Scheme

(1S,5S,6S,7S,8S,12S)-6-((R)-2-Hydroxy-1-methylene-pent-4-enyl)-7,11,14,14-tetramethyl-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-ene-3,9-dione (187961-07-5) → 10-deacetylbaccatin III (32981-86-5)

Conditions	Yield
Multi-step reaction with 10 steps 1: N,N-diisopropylethylamine / 55 °C 2: NH4F / methanol / 20 °C 3: tetrahydrofuran / -78 °C 4: imidazole / CHCl3 5: 92 percent / pyridine / CH2Cl2 6: 76 percent / KCN / ethanol / 0 °C 7: 95 percent / (i-Pr)2NEt / toluene / 110 °C 8: 89 percent / DMAP 9: 96 percent / TASF / tetrahydrofuran / 0 °C 10: tetrahydrofuran / -78 °C View Scheme

10-deacetylbaccatin III (32981-86-5) + triethylsilyl chloride (994-30-9) → 7-triethylsilyl-10-deacetylbaccatin III (115437-18-8)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide	100%
With pyridine Ambient temperature;	98%
In pyridine at 25℃; for 24h;	97.7%

10-deacetylbaccatin III (32981-86-5) → 10-deacetyl-2-(hexahydro)baccatin III (158660-66-3)

Conditions	Yield
With hydrogen; Rh on carbon In methanol at 35℃; under 25857.4 Torr; for 24h;	100%

10-deacetylbaccatin III (32981-86-5) + Acetyl bromide (506-96-7) + Trichloroacetyl chloride (76-02-8) → 7-trichloroacetylbaccatin III (204124-97-0)

Conditions	Yield
Stage #1: 10-deacetylbaccatin III; trifluoroacetyl chloride With pyridine In chloroform at 35℃; for 4h; Stage #2: Acetyl bromide In chloroform at 20℃; for 5h;	100%
Stage #1: 10-deacetylbaccatin III; trifluoroacetyl chloride With pyridine In chloroform at 35℃; for 4h; Stage #2: Acetyl bromide In chloroform at 20℃; for 5h;	100%

10-deacetylbaccatin III (32981-86-5) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → 7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III (95603-44-4)

Conditions	Yield
With pyridine In dichloromethane at 50℃; under 7500.75 Torr; for 0.0277778h; Concentration; Temperature; Pressure;	98.4%
With pyridine In dichloromethane at 2℃; for 2h; Temperature;	98.9%
With pyridine at 0 - 20℃;	91%

10-deacetylbaccatin III (32981-86-5) + acetic anhydride (108-24-7) → baccatin III (27548-93-2)

Conditions	Yield
lanthanum(lll) triflate In tetrahydrofuran for 2h;	97%
With cerium(III) chloride heptahydrate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Cooling with ice;	96%
With cerium(III) chloride heptahydrate In tetrahydrofuran at 20℃; for 2h;	94.4%

10-deacetylbaccatin III (32981-86-5) + acetic anhydride (108-24-7) → 7,13-diacetyl baccatin III (92950-44-2)

Conditions	Yield
With dmap In pyridine at 23℃; for 20h; Inert atmosphere;	96%
In pyridine at 80℃; for 24h;	30 mg

10-deacetylbaccatin III (32981-86-5) + triethylsilyl chloride (994-30-9) → 7,10,13-tris(triethylsilyl)-10-deacetylbaccatin III (194720-19-9)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 40h; silylation;	96%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 47h; silylation;	96%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	96%

10-deacetylbaccatin III (32981-86-5) + 2-Methylpropionic anhydride (97-72-3) → 10-isobutyloyl 10-deacetylbaccatin III (207680-02-2)

Conditions	Yield
lanthanum(lll) triflate In tetrahydrofuran	96%
With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In tetrahydrofuran; chloroform at -40℃; for 48h;	89%
With cerium(III) chloride In tetrahydrofuran at 20℃; for 4h;

10-deacetylbaccatin III (32981-86-5) + benzyl chloroformate (501-53-1) → C-7,C-10-dibenzyloxycarbonyl-10-deacetyl baccatin III (194864-02-3)

Conditions	Yield
With dmap In tetrahydrofuran at 40 - 50℃;	96%
With dmap In tetrahydrofuran at 40 - 60℃; for 1.5h;	81%
With n-hexyllithium In tetrahydrofuran at -44 - 40℃;

10-deacetylbaccatin III (32981-86-5) → 10-dehydro-10-deacetylbaccatin III (V) (191276-24-1)

Conditions	Yield
With copper diacetate In methanol	95%

10-deacetylbaccatin III (32981-86-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → (1S,2S,3R,4S,5R,7S,8S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-10-formyloxy-9-oxo-1,7,13-trihydroxytax-11-ene (184586-78-5)

Conditions	Yield
With dmap; trifluoromethylsulfonic anhydride at 0℃;	95%
With dmap; trifluoromethylsulfonic anhydride for 0.166667h;	95%
With pyridine; trifluoromethylsulfonic anhydride; water 1.) -20 deg C, 10 min; 2.) 0 deg C, 3 h; Yield given. Multistep reaction;

10-deacetylbaccatin III (32981-86-5) + chloroacetyl chloride (79-04-9) → 7,10-di-O-chloroacetyl-10-deacetylbaccatin III (500726-10-3)

Conditions	Yield
With pyridine; dmap In dichloromethane at 25 - 30℃; for 0.5h;	95%
Stage #1: 10-deacetylbaccatin III With pyridine; dmap In dichloromethane for 0.166667h; Stage #2: chloroacetyl chloride In dichloromethane at 25 - 30℃; for 0.333333h;	95%
With pyridine; dmap In dichloromethane at -5 - 5℃; for 2h; Inert atmosphere;
Stage #1: 10-deacetylbaccatin III With pyridine; dmap In dichloromethane for 0.166667h; Stage #2: chloroacetyl chloride In dichloromethane at 5 - 10℃; for 2h;

10-deacetylbaccatin III (32981-86-5) + di-tert-butyl dicarbonate (24424-99-5) → 7,10,13-tri-Boc-10-deacetylbaccatin (1353716-43-4)

Conditions	Yield
With dmap In tetrahydrofuran; dichloromethane at 20℃; for 12h; Inert atmosphere;	95%

10-deacetylbaccatin III (32981-86-5) + N,O-bis(triethylsilyl) trifluoroacetamide (207680-13-5) → 10-deacetyl-10-triethylsiloxybaccatin III

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 0℃; for 0.0833333h; Inert atmosphere;	95%

N,O-bis-trimethylsilyl-trifluoromethyl-acetamide + 10-deacetylbaccatin III (32981-86-5) → 10-trimethylsilyl-10-deacetyl baccatin III (207680-14-6)

Conditions	Yield
Stage #1: N,O-bis-trimethylsilyl-trifluoromethyl-acetamide; 10-deacetylbaccatin III In tetrahydrofuran at 25℃; Stage #2: With lithium hexamethyldisilazane In tetrahydrofuran for 0.416667h;	93%

10-deacetylbaccatin III (32981-86-5) + 3,5-dinitrobenoyl chloride (99-33-2) → 7,10-(di-3',5'-dinitrobenzoyl)-10-deacetylbaccatin III (1033517-17-7) + 10-(3',5'-dinitrobenzoyl)-10-deacetylbaccatin III (1033517-21-3) + 7-(3',5'-dinitrobenzoyl)-10-deacetylbaccatin III (1033517-19-9) + 7,10,13-(tri-3',5'-dinitrobenzoyl)-10-deacetylbaccatin III (1033517-23-5)

Conditions	Yield
With pyridine In chloroform at 38 - 42℃;	A 93% B n/a C n/a D 0.9%

10-deacetylbaccatin III (32981-86-5) → (2aR,4S,4aS,8R,11S,12S,12aR,12bS,Z)-12b-acetoxy-4,11-dihydroxy-4a,8,13,13-tetramethyl-5,9-dioxo-2a,3,4,4a,5,8,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Conditions	Yield
With diethylamino-sulfur trifluoride In tetrahydrofuran at -78℃; for 3h; Molecular sieve; Inert atmosphere;	93%

10-deacetylbaccatin III (32981-86-5) + cinnamic anhydride (21947-71-7) → 10-O-cinnamoyl-10-deacetylbaccatin III

Conditions	Yield
With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In tetrahydrofuran; chloroform at -20℃; for 72h;	93%

10-deacetylbaccatin III (32981-86-5) → 13-dehydro-10-deacetylbaccatin III (92950-42-0)

Conditions	Yield
With ozone In methanol; dichloromethane at -78℃; for 0.583333h;	92%
With pyridinium chlorochromate In dichloromethane for 0.75h; Ambient temperature;	79%
With periodic acid In 1,4-dioxane for 72h; Ambient temperature;	75%
With 3-chloro-benzenecarboperoxoic acid In ethyl acetate for 24h; Ambient temperature;

10-deacetylbaccatin III (32981-86-5) + acetic anhydride (108-24-7) → 7-O-acetylbaccatine III (32981-90-1)

Conditions	Yield
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In tetrahydrofuran at 10℃; for 1h; Reagent/catalyst; Solvent; Temperature; Concentration; Inert atmosphere;	91.8%

10-deacetylbaccatin III (32981-86-5) → 10-dehydro 10-deacetyl 7-epibaccatin V (92950-45-3)

Conditions	Yield
With triethylamine; copper dichloride In ethanol; ethyl acetate at -13 - -1.3℃; for 1h;	91.3%
Stage #1: 10-deacetylbaccatin III With triethylamine; copper dichloride In ethanol; ethyl acetate at -17.6 - -1.3℃; for 1h; Stage #2: With trifluoroacetic acid In ethanol; ethyl acetate for 0.25h; Product distribution / selectivity;
Stage #1: 10-deacetylbaccatin III With triethylamine; copper dichloride In ethanol; ethyl acetate at -13 - -1.3℃; Inert atmosphere; Stage #2: With trifluoroacetic acid In ethanol; ethyl acetate for 0.25h;
With triethylamine; copper dichloride In ethanol; ethyl acetate at -13℃; for 1h; Inert atmosphere;
Stage #1: 10-deacetylbaccatin III With triethylamine; copper dichloride In ethanol; ethyl acetate at -13 - -1.3℃; for 1h; Stage #2: With trifluoroacetic acid In ethanol; ethyl acetate for 0.25h;

10-deacetylbaccatin III (32981-86-5) + tert-butyldimethylsilyl chloride (18162-48-6) → 7-triethylsilyl-10-deacetylbaccatin III (115437-18-8)

Conditions	Yield
With pyridine at 25℃; for 17h;	91%

10-deacetylbaccatin III (32981-86-5) + benzoic acid anhydride (93-97-0) → 10-O-benzoyl-10-deacetylbaccatin III (207680-03-3)

Conditions	Yield
lanthanum(lll) triflate In tetrahydrofuran	91%
With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In tetrahydrofuran; chloroform at -20℃; for 168h;	84%
With cerium(III) chloride In tetrahydrofuran at 20℃; for 4h;

10-deacetylbaccatin III (32981-86-5) + triisopropylsilyl chloride (13154-24-0) → C38H56O10Si

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 23h;	90.8%

10-deacetylbaccatin III (32981-86-5) + p-toluenesulfonyl chloride (98-59-9) → C43H48O14S2

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 4h;	90%

10-deacetylbaccatin III (32981-86-5) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → C31H37Cl3O10

Conditions	Yield
With pyridine In dichloromethane at 35℃; for 27h;	89.7%

10-deacetylbaccatin III (32981-86-5) + carbonic acid dimethyl ester (616-38-6) → 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene (183133-94-0)

Conditions	Yield
With dmap; caesium bromide; sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at -30℃; for 3h; Temperature; Reagent/catalyst;	89.6%

10-deacetylbaccatin III (32981-86-5) + triethylsilyl chloride (994-30-9) → 7,10-bis(triethylsilyl)-10-deacetylbaccatin III (149107-84-6)

Conditions	Yield
Stage #1: 10-deacetylbaccatin III; triethylsilyl chloride With dmap; triethylamine In tetrahydrofuran at 25℃; Inert atmosphere; Stage #2: With lithium bromide In tetrahydrofuran at 20 - 70℃; Inert atmosphere;	89%
Stage #1: 10-deacetylbaccatin III; triethylsilyl chloride With dmap; triethylamine In tetrahydrofuran at 20℃; for 5.5h; Inert atmosphere; Stage #2: With lithium bromide In tetrahydrofuran at 65 - 70℃; for 7h;	84%
Stage #1: 10-deacetylbaccatin III; triethylsilyl chloride With dmap; triethylamine In tetrahydrofuran at 20℃; for 5.5h; Inert atmosphere; Stage #2: With lithium bromide In tetrahydrofuran at 65 - 70℃; for 7h;	84%

Upstream product

• 289703-22-6 10-deacetylbaccatin III 7,10-bis-trichloroacetate 
• 591-51-5 phenyllithium 
• 187961-12-2 C₂₈H₃₃Cl₃O₁₃ 
• 71629-92-0 10-deacetyl-7-epi-baccatin III 
• 27548-93-2 baccatin III 
• 33069-62-4 taxol 
• 148930-54-5 (2aR,4S,4aS,6R,9S,11S,12S,12bS)-6,12b-bis(acetyloxy)-9-({(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl}oxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9, 10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate 
• 115437-18-8 7-triethylsilyl-10-deacetylbaccatin III 
• 71610-00-9 Cephalomannine 
• 90332-63-1 7-O-(β-xylosyl)-10-deacetyltaxol 
• 157664-03-4 7-β-D-xylosylbaccatin III 
• 197013-82-4 7-α-glucosyloxyacetyl paclitaxel 
• 32981-90-1 7-O-acetylbaccatine III 
• 500726-11-4 7-O-chloroacetylbaccatin III 

Downstream Products

• 92950-41-9 7-acetyl-10-deacetyl baccatin III 
• 32981-90-1 7-O-acetylbaccatine III 
• 92950-44-2 7,13-diacetyl baccatin III 
• 103150-33-0 7-(2,2,2-trichloroethyloxycarbonyl)baccatin III 
• 110258-92-9 7,10,13-tri(2,2,2-tricholoroethyloxycarbonyl)-10-deacetyl baccatin III 
• 95603-44-4 7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III 
• 71629-92-0 10-deacetyl-7-epi-baccatin III 
• 150930-84-0 10-desacetoxybaccatin 
• 27548-93-2 baccatin III 
• 194720-19-9 7,10,13-tris(triethylsilyl)-10-deacetylbaccatin III 
• 27548-93-2 baccatin III 
• 162475-68-5 10-deacetyl-9β-dihydrobaccatin III 
• 207680-01-1 C₃₃H₄₂O₁₁ 
• 114977-29-6 2'-epi 3'-epi N-debenzoyl-N-tert-butoxycarbonyl-10-deacetyl taxol 

Relevant articles and documents

Glycosyl hydrolase with beta-xylosidase and beta-glucosidase activities and uses thereof

A novel glycosyl hydrolase with activities of beta-xylosidase and beta-glucosidase is provided. Said glycosyl hydrolase can convert 7-xylosyltaxane compounds to 7-hydroxyltaxane compounds.

Microbial transformation of 7-epi-10-deacetylbaccatin III to 10-deacetylbaccatin III

The microbial transformation of 7-epi-10-deacetylbaccatin III (7-epi-10-DAB III) to 10-deacetylbaccatin III (10-DAB III) was studied. In this report, seven microorganisms were found to be able to realize the transformation at yields from 20.0% to as high as 70.8%. The optimized conditions such as the solvent, pH value of the medium, the microorganisms, transformation time, and substrate concentration were investigated.

Biological degradation of taxol by action of cultured cells on 7-acetyltaxol-2″-yl glucoside

Biodegradation pathways of taxol in cultured cells of Synechocystis sp. PCC 6803, Synechococcus sp. PCC 7942, Marchantia polymorpha, Nicotiana tabacum, and Glycine max were investigated using a water-soluble taxol derivative, 7-ace-tyltaxol-2″-yl glucoside, as the substrate. Although cyanobacteria, Synechocystis sp. PCC 6803 and Synechococcus sp. PCC 7942, and a lower plant, M. polymorpha, catalyzed the epimerization at 7-position of taxol skeleton, no epimerization occurred with higher plants, N. tabacum and G. max. On the other hand, Synechocystis sp. PCC 6803, Synechococcus sp. PCC 7942, M. polymorpha, and N. tabacum catalyzed hydrolysis at 13-position of taxol to give baccatin III and 10-deacetyl baccatin III. Both cyanobacteria cells also deacetylated 7-epi-baccatin III at its 10-position. M. polymorpha and G. max deacetylated at 10-position of taxol. Copyright