(3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbothioic acid S-ethyl ester

Base Information

Chemical Name:(3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbothioic acid S-ethyl ester
CAS No.:929118-82-1
Molecular Formula:C₃₃H₄₆O₄SSi
Molecular Weight:566.877
Hs Code.:

(3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbothioic acid S-ethyl ester

Synonyms:(3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbothioic acid S-ethyl ester

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Chemical Property of (3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbothioic acid S-ethyl ester

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Technology Process of (3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbothioic acid S-ethyl ester

There total 7 articles about (3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbothioic acid S-ethyl ester 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: 94.0%

: 929118-81-0
(S)-1-benzyl-3-[(3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbonyl]-oxazolidin-2-one

: 75-08-1
ethanethiol

: 929118-82-1
(3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbothioic acid S-ethyl ester

Guidance literature:: ethanethiol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃;

(S)-1-benzyl-3-[(3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbonyl]-oxazolidin-2-one; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;
DOI:10.1021/ja0684996

Reference yield:

: 929118-79-6
(S)-4-benzyl-3-[(1R,2S,4aR,8aS)-2-(tert-butyl-diphenyl-silanyloxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbonyl]-oxazolidin-2-one

: 929118-82-1
(3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbothioic acid S-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 92 percent / K₂OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 60 h / pH 7.0

2.1: 90 percent / p-toluenesulfonic acid hydrate / acetone / 1.5 h

3.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

3.2: 94 percent / tetrahydrofuran; hexane / 0.5 h / 0 °C

With potassium osmate(VI); n-butyllithium; N-methyl-2-indolinone; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; acetone; tert-butyl alcohol;
DOI:10.1021/ja0684996

Reference yield:

: 929118-78-5
(S)-4-benzyl-3-[(2E,8E,10E)-12-(tert-butyl-diphenyl-silanyloxy)-dodeca-2,8,10-trienoyl]-oxazolidin-2-one

: 929118-82-1
(3aS,4S,5R,5aS,9aS,9bR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-decahydro-naphtho[1,2-d][1,3]dioxole-5-carbothioic acid S-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 81 percent / Me₂AlCl / CH₂Cl₂ / 1.5 h / -78 - -30 °C

2.1: 92 percent / K₂OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 60 h / pH 7.0

3.1: 90 percent / p-toluenesulfonic acid hydrate / acetone / 1.5 h

4.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

4.2: 94 percent / tetrahydrofuran; hexane / 0.5 h / 0 °C

With potassium osmate(VI); n-butyllithium; N-methyl-2-indolinone; dimethylaluminum chloride; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; acetone; tert-butyl alcohol; 1.1: Diels-Alder cycloaddition;
DOI:10.1021/ja0684996