(3β,5α,6β,15α,17β)-17-tert-Butyldimethylsilyloxy-6-methoxy-3,5-cycloandrostan-15-ol

Base Information

• Chemical Name: (3β,5α,6β,15α,17β)-17-tert-Butyldimethylsilyloxy-6-methoxy-3,5-cycloandrostan-15-ol
• CAS No.: 61252-35-5
• Molecular Formula: C₂₆H₄₆O₃Si
• Molecular Weight: 434.735
• Mol file: 61252-35-5.mol

Synonyms:(3β,5α,6β,15α,17β)-17-tert-Butyldimethylsilyloxy-6-methoxy-3,5-cycloandrostan-15-ol;(3β,5α,6β,15α,17β)-17-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-6-Methoxy-3,5-cycloandrostan-15-ol

Chemical Property of (3β,5α,6β,15α,17β)-17-tert-Butyldimethylsilyloxy-6-methoxy-3,5-cycloandrostan-15-ol

Chemical Property:

• Boiling Point: 472.8±40.0 °C(Predicted)
• PKA: 14.50±0.70(Predicted)
• PSA: 38.69000
• Density: 1.05±0.1 g/cm3(Predicted)
• LogP: 6.01520
• Solubility.: Chloroform, Dichloromethane, Ether, Ethyl Acetate

Purity/Quality:

97% ^*data from raw suppliers

(3β,5α,6β,15α,17β)-17-tert-Butyldimethylsilyloxy-6-methoxy-3,5-cycloandrostan-15-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3β,5α,6β,15α,17β)-17-tert-Butyldimethylsilyloxy-6-methoxy-3,5-cycloandrostan-15-ol

There total 2 articles about (3β,5α,6β,15α,17β)-17-tert-Butyldimethylsilyloxy-6-methoxy-3,5-cycloandrostan-15-ol 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:

Toluene-4-sulfonic acid (3S,8R,9S,10R,13S,17S)-17-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester → (1aR,3aR,3bS,5aS,6S,8S,8aS,8bR,10R,10aR)-6-(tert-Butyl-dimethyl-silanyloxy)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-8-ol (61252-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1: KOAc

2: (i) B₂H₆, THF, (ii) aq. H₂O₂, NaOH

With potassium acetate;

DOI:10.1248/cpb.24.1860

Reference yield:

tert-Butyl-((1aR,3aR,3bS,5aS,6S,8bR,10R,10aR)-10-methoxy-3a,5a-dimethyl-1,1a,2,3,3a,3b,4,5,5a,6,7,8b,9,10-tetradecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yloxy)-dimethyl-silane → (1aR,3aR,3bS,5aS,6S,8S,8aS,8bR,10R,10aR)-6-(tert-Butyl-dimethyl-silanyloxy)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-8-ol (61252-35-5) + (1aR,3aR,3bS,5aS,6S,8R,8aR,8bR,10R,10aR)-6-(tert-Butyl-dimethyl-silanyloxy)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-8-ol

Guidance literature:

Multistep reaction; (i) B₂H₆, THF, (ii) aq. H₂O₂, NaOH;

DOI:10.1248/cpb.24.1860

Reference yield:

(1aR,3aR,3bS,5aS,6S,8S,8aS,8bR,10R,10aR)-6-(tert-Butyl-dimethyl-silanyloxy)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-8-ol (61252-35-5) → 15alpha-Hydroxytestosterone (2226-70-2)

Guidance literature:

Multi-step reaction with 4 steps

1: (i) BF₃-Et₂O, THF, Et₂O, (ii) /BRN= 505999/, imidazole, DMF

2: aq. KOH / methanol; tetrahydrofuran

3: Al(OiPr)3, MeCOEt / benzene

4: aq. HCl / acetone

With hydrogenchloride; potassium hydroxide; aluminum isopropoxide; butanone; In tetrahydrofuran; methanol; acetone; benzene;

DOI:10.1248/cpb.25.2650

Downstream raw materials:

3β-Acetoxy-5-androsten-15α,17β-diol-bis-(tert.-butyldimethylsilyl)-ether

15alpha-Hydroxytestosterone

5-Androsten-3β,15α,17β-triol-15,17-bis-(tert.-butyldimethylsilyl)-ether

15α,17β-Dihydroxy-4-androsten-3-on-bis-(tert.-butyldimethylsilyl)-ether

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