15-[1-(4,5-Dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one

Base Information

• Chemical Name: 15-[1-(4,5-Dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
• CAS No.: 30655-48-2
• Molecular Formula: C₂₈H₃₈O₆
• Molecular Weight: 470.606
• NSC Number: 179841
• DSSTox Substance ID: DTXSID40865554
• Wikidata: Q105249107
• Mol file: 30655-48-2.mol

Synonyms:NSC179841;DTXSID40865554;4,20-Dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione

Chemical Property of 15-[1-(4,5-Dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one

Chemical Property:

• Vapor Pressure: 1.92E-20mmHg at 25°C
• Melting Point: 253-255 °C
• Boiling Point: 663.7°Cat760mmHg
• PKA: 13.49±0.70(Predicted)
• Flash Point: 220.3°C
• PSA: 96.36000
• Density: 1.28g/cm³
• LogP: 3.49540
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 470.26683893
• Heavy Atom Count: 34
• Complexity: 1030

Purity/Quality:

99% ^*data from raw suppliers

WithanolideD ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)O)C

Technology Process of 15-[1-(4,5-Dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one

There total 20 articles about 15-[1-(4,5-Dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one 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: 72.0%

(20R,22R)-4β,20-dihydroxy-1-oxowitha-2,5,24-trienolide (90525-29-4) → withanolide D (30655-48-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; for 6h; Ambient temperature;

Reference yield:

Pregnenolone (145-13-1) → withanolide D (30655-48-2)

Guidance literature:

Multi-step reaction with 20 steps

1: 28 g / NaBH₄ / methanol; tetrahydrofuran / 0.67 h / 0 °C

2: 61 percent / dichlorodicyanobenzoquinone / dioxane / 8 h / Heating

3: toluene-p-sulphonic acid / CH₂Cl₂ / 3 h / Ambient temperature

4: 83 percent / 30percent H₂O₂, NaOH / methanol / 15 °C

5: 1.) liquid NH₃, Li, 2.) NH₄Cl / 1.) THF, -78 deg C -> -40 deg C, 20 min, 2.) 2 h

6: N,N-diethylcyclohexylamine / dioxane / 6 h / Heating

7: 2M HCl / methanol / 2 h / Ambient temperature

8: 80 percent / pyridinium chlorochromate, AcONa / CH₂Cl₂ / 3 h / Ambient temperature

9: 1.) n-BuLi / 1.) THF, - 5 deg C, 2.) -5 deg C, 8 h

10: 85 percent / HgO, BF₃-ether / tetrahydrofuran / 0.5 h / Heating

11: 81 percent / N,N-diethylcyclohexylamine / dioxane / 8 h / Heating

12: 1.) LDA, HMPA / 1.) THF, - 78 deg C, 1 h, 2.) -78 deg C, 6 h

13: 82 percent / 6M HCl / tetrahydrofuran / 3 h / Ambient temperature

14: 90 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

15: 76 percent / m-chloroperbenzoic acid / CHCl₃ / 0.67 h / -5 °C

16: 80 percent / pyridinium dichromate / dimethylformamide / 8 h / -5 °C

17: 1.) alumina Woelm N-20 / 1.) Et₂O, room tempereature, 20 min, 2.) Et₂O-THF, room temperature, 2 h

18: 84 percent / TsOH*H₂O / benzene / 1 h / 60 °C

19: 1.) m-chloroperbenzoic acid, 2.) trimethyl phosphite / 1.) CHCl₃, -78 deg C, 10 min, 2.) MeOH, THF, room temperature, 10 h

20: 72 percent / m-chloroperbenzoic acid / CHCl₃ / 6 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; aluminum oxide; sodium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; diethyl-cyclohexyl-amine; boron trifluoride diethyl etherate; ammonia; dihydrogen peroxide; sodium acetate; lithium; ammonium chloride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury(II) oxide; lithium diisopropyl amide; phosphorous acid trimethyl ester; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene;

Reference yield:

3β,20-dihydroxypregn-5-ene (59042-34-1) → withanolide D (30655-48-2)

Guidance literature:

Multi-step reaction with 19 steps

1: 61 percent / dichlorodicyanobenzoquinone / dioxane / 8 h / Heating

2: toluene-p-sulphonic acid / CH₂Cl₂ / 3 h / Ambient temperature

3: 83 percent / 30percent H₂O₂, NaOH / methanol / 15 °C

4: 1.) liquid NH₃, Li, 2.) NH₄Cl / 1.) THF, -78 deg C -> -40 deg C, 20 min, 2.) 2 h

5: N,N-diethylcyclohexylamine / dioxane / 6 h / Heating

6: 2M HCl / methanol / 2 h / Ambient temperature

7: 80 percent / pyridinium chlorochromate, AcONa / CH₂Cl₂ / 3 h / Ambient temperature

8: 1.) n-BuLi / 1.) THF, - 5 deg C, 2.) -5 deg C, 8 h

9: 85 percent / HgO, BF₃-ether / tetrahydrofuran / 0.5 h / Heating

10: 81 percent / N,N-diethylcyclohexylamine / dioxane / 8 h / Heating

11: 1.) LDA, HMPA / 1.) THF, - 78 deg C, 1 h, 2.) -78 deg C, 6 h

12: 82 percent / 6M HCl / tetrahydrofuran / 3 h / Ambient temperature

13: 90 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

14: 76 percent / m-chloroperbenzoic acid / CHCl₃ / 0.67 h / -5 °C

15: 80 percent / pyridinium dichromate / dimethylformamide / 8 h / -5 °C

16: 1.) alumina Woelm N-20 / 1.) Et₂O, room tempereature, 20 min, 2.) Et₂O-THF, room temperature, 2 h

17: 84 percent / TsOH*H₂O / benzene / 1 h / 60 °C

18: 1.) m-chloroperbenzoic acid, 2.) trimethyl phosphite / 1.) CHCl₃, -78 deg C, 10 min, 2.) MeOH, THF, room temperature, 10 h

19: 72 percent / m-chloroperbenzoic acid / CHCl₃ / 6 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; aluminum oxide; sodium hydroxide; dipyridinium dichromate; n-butyllithium; diethyl-cyclohexyl-amine; boron trifluoride diethyl etherate; ammonia; dihydrogen peroxide; sodium acetate; lithium; ammonium chloride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury(II) oxide; lithium diisopropyl amide; phosphorous acid trimethyl ester; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene;

upstream raw materials:

(20R,22R)-4β,20-dihydroxy-1-oxowitha-2,5,24-trienolide

Pregnenolone

3β,20-dihydroxypregn-5-ene

20ξ-hydroxypregna-1,4,6-trien-3-one

Refernces