(8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnane

Base Information

Chemical Name:(8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnane
CAS No.:946132-18-9
Molecular Formula:C₃₀H₅₀O₃Si
Molecular Weight:486.811
Hs Code.:

Synonyms:(8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnane

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Chemical Property of (8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnane

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Technology Process of (8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnane

There total 7 articles about (8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnane 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: 98.0%

: 946132-16-7
(8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-hydroxy-pentyl]-pregnane

: 69739-34-0
t-butyldimethylsiyl triflate

: 946132-18-9
(8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -20 - 0 ℃; for 1h;

Reference yield:

: 66774-71-8
Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester

: 946132-18-9
(8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnane

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -20 °C

1.2: 22 h / -20 - 20 °C

2.1: palladium 10% on activated carbon; hydrogen / methanol

3.1: 2,6-dimethylpyridine / dichloromethane / -20 - 0 °C

With 2,6-dimethylpyridine; n-butyllithium; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; dichloromethane; 1.1: Wittig reaction / 1.2: Wittig reaction;
DOI:10.1021/jm1010447

Reference yield:

: 66774-70-7
(8S,20S)-des-A,B-8-benzoyloxy-20-(hydroxymethyl)-pregnane

: 946132-18-9
(8S,20R)-des-A,B-8-benzoyloxy-20-[(4'S)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnane

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 1 h / -20 °C

2.2: 22 h / -20 - 20 °C

3.1: palladium 10% on activated carbon; hydrogen / methanol

4.1: 2,6-dimethylpyridine / dichloromethane / -20 - 0 °C

With 2,6-dimethylpyridine; n-butyllithium; palladium 10% on activated carbon; hydrogen; sulfur trioxide pyridine complex; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 2.1: Wittig reaction / 2.2: Wittig reaction;
DOI:10.1021/jm1010447