beta-Peltatin

Base Information

• Chemical Name: beta-Peltatin
• CAS No.: 518-29-6
• Molecular Formula: C22H22O8
• Molecular Weight: 414.412
• NSC Number: 35471,24819
• UNII: 3U9W61G72Y
• DSSTox Substance ID: DTXSID10199732
• Nikkaji Number: J6.583H
• Wikidata: Q27144976
• Metabolomics Workbench ID: 143570
• ChEMBL ID: CHEMBL97543
• Mol file: 518-29-6.mol

Synonyms:beta-Peltatin;518-29-6;beta-Peltatin A;PELTATIN B;Peltatin methyl ether;PELTATIN, BETA;(-)-beta-peltatin;PELTATIN;(-)-|A-Peltatin;.beta.-Peltatin;alpha-Peltalin A;NSC 24819;BRN 0099483;AI3-50532;NSC24819;UNII-3U9W61G72Y;CHEBI:74867;3U9W61G72Y;NSC35471;.beta.-Peltatin A;.alpha.-Peltalin A;NSC-24819;NSC-35471;(5aR,8aR,9R)-4-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one;5-19-10-00670 (Beilstein Handbook Reference);Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-10-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R-(5alpha,5abeta,8aalpha))-;MLS002702982;beta-peltatin-a;Peltatin, beta-;Furo[3',7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-10-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,5a.beta.,8a.alpha.)]-;.beta.-Peltatin-B;Spectrum_001780;Spectrum3_001096;Spectrum4_001925;Spectrum5_001882;BSPBio_002772;KBioGR_002270;KBioSS_002261;CHEMBL97543;SCHEMBL516627;SPECTRUM1504739;.BETA.-PELTATIN [MI];(-)-.BETA.-PELTATIN;KBio2_002260;KBio2_004828;KBio2_007396;KBio3_001992;DTXSID10199732;.BETA.-PELTATIN, (-)-;Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-10-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,5a.beta.,8a.alpha.)]-;AKOS040762170;SDCCGMLS-0066768.P001;NCGC00161926-01;NCGC00161926-02;NCI60_001982;XP178053;HY-125135;LS-101359;CS-0089444;BRD-K13265046-001-02-1;Q27144976;(5aR,8aR,9R)-4-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one;(5R,5aR,8aR)-10-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one;(5R,5AR,8AR)-5,8,8A,9-TETRAHYDRO-10-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)FURO(3,4:6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE;FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE, 5,8,8A,9-TETRAHYDRO-10-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)-, (5R,5AR,8AR)-;Naphtho[2,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-9-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-, .gamma.-lactone

Chemical Property of beta-Peltatin

Chemical Property:

• Melting Point: 234 °C
• Boiling Point: 586.8°Cat760mmHg
• PKA: 9.49±0.40(Predicted)
• Flash Point: 205.8°C
• PSA: 92.68000
• Density: 1.363g/cm³
• LogP: 2.62390
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 414.13146766
• Heavy Atom Count: 30
• Complexity: 629

Purity/Quality:

98% min ^*data from raw suppliers

β-Peltatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(CC4=C(C5=C(C=C24)OCO5)O)COC3=O
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@@H](CC4=C(C5=C(C=C24)OCO5)O)COC3=O
• Uses: β-Peltatin is one of the major lignans in Podophyllum peltatum, and is one of the components of Podophyllin, a complex mixture of oils and pigments that was used as a purgative. β-Peltatin also has biological activity against tumours.

Technology Process of beta-Peltatin

There total 29 articles about beta-Peltatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(5aR,8aR)-10-Benzyloxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (82299-45-4) → (+/-)-iso β-peltatine (477-50-9,518-29-6,641-25-8,82336-50-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 18h; under 3800 Torr;

DOI:10.1016/S0040-4039(00)86991-9

Reference yield: 80.0%

O-benzyl (+/-)-iso-β-peltatine (82299-45-4) → (+/-)-iso-β-peltatine (477-50-9,518-29-6,641-25-8,82336-50-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 18h; under 3750.3 Torr; Ambient temperature;

DOI:10.1016/S0040-4020(01)83505-5

Reference yield:

2H-benzo[d]1,3-dioxolane-4-carbaldehyde (7797-83-3) → (+/-)-iso-β-peltatine (477-50-9,518-29-6,641-25-8,82336-50-3)

Guidance literature:

Multi-step reaction with 12 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 36 h / Heating

2: 10percent KOH / methanol / 1.5 h / Ambient temperature

3: 98 percent / trifluoroacetate d argent, brome / CHCl₃ / 0.5 h / Ambient temperature

4: 1.) 1.6M n-BuLi / 1.) hexane, ether, reflux, 1.75 h; 2.) reflux, 45 min

5: 97 percent / K₂CO₃, NaI / ethanol / 16 h / Heating

6: 75 percent / NaOMe / methanol / 6 h / Heating

7: 1.) 2N KOH; 2.) CaCl₂, NaBH₄, 2.5M KOH / 1.) water; 2.) ethanol, 50 deg C, 1 h

8: 86 percent / H₂ / 5percent Pd/C / ethyl acetate / 18 h / 3800 Torr / Ambient temperature

9: 84 percent / K₂CO₃, NaI / acetone / 16 h / Heating

10: 71.25 percent / hexamethyldisilylamine, 1.6M n-BuLi / hexane; benzene / 0.05 h / 5 - 10 °C

11: 88 percent / trifluoroacetic acid / CH₂Cl₂ / 6 h / Ambient temperature

12: 80 percent / H₂ / 10percent Pd/C / ethyl acetate / 18 h / 3750.3 Torr / Ambient temperature

With potassium hydroxide; sodium tetrahydroborate; n-butyllithium; trifluoroacetate d argent; hydrogen; bromine; sodium methylate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; sodium iodide; calcium chloride; palladium on activated charcoal; In methanol; ethanol; hexane; dichloromethane; chloroform; ethyl acetate; acetone; benzene;

DOI:10.1016/S0040-4020(01)83505-5

upstream raw materials:

deoxypodophyllotoxin

(5aR,8aR)-10-Benzyloxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

2H-benzo[d]1,3-dioxolane-4-carbaldehyde

benzyloxy-2 piperonal

Downstream raw materials:

(-)-β-peltatin-A-methyl ether

β-peltatin B methyl ether

O-Acetyl-β-peltatin-B

8-O-(β-Cellobiosyl)-β-peltatin-A

Refernces

• 1、 Loriot,Robin,Brown. "Total synthesis and study of biologically active lignans. VI. Total synthesis of (±)-iso-β-peltatine and analogs". . p. 2529 - 2535. Retrieved 2007/10/02.