(1S,3aS,5S,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a,5-diol

Base Information

Chemical Name:(1S,3aS,5S,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a,5-diol
CAS No.:392235-12-0
Molecular Formula:C₂₃H₃₈O₄Si
Molecular Weight:406.638
Hs Code.:

Synonyms:(1S,3aS,5S,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a,5-diol

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Chemical Property of (1S,3aS,5S,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a,5-diol

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Technology Process of (1S,3aS,5S,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a,5-diol

There total 3 articles about (1S,3aS,5S,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a,5-diol 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: 61.0%

: 65423-56-5
1-bromo-3-[(tert-butyldimethylsilyl)oxy]benzene

: 178379-39-0
(1S,3aS,7aR)-1-hydroxymethyl-3a-hydroxy-7a-methyl-5-perhydroindenone

: 392235-12-0
(1S,3aS,5S,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a,5-diol

Guidance literature:: 1-bromo-3-[(tert-butyldimethylsilyl)oxy]benzene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - 0 ℃; for 1.33333h;

(1S,3aS,7aR)-1-hydroxymethyl-3a-hydroxy-7a-methyl-5-perhydroindenone; In tetrahydrofuran; diethyl ether; pentane; at -78 ℃; for 0.5h; Further stages.;
DOI:10.1021/jm011001k

Reference yield:

: 162240-26-8
C₁₃H₂₀O₄

: 392235-12-0
(1S,3aS,5S,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a,5-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaBH₄ / 2.5 h / -20 °C

2.1: 68 percent / 1 N pTSA / acetonitrile; H₂O / 16 h

3.1: tert-butyllithium / diethyl ether; pentane / 1.33 h / -78 - 0 °C

3.2: 61 percent / diethyl ether; pentane; tetrahydrofuran / 0.5 h / -78 °C

With sodium tetrahydroborate; tert.-butyl lithium; toluene-4-sulfonic acid; In diethyl ether; water; acetonitrile; pentane;
DOI:10.1021/jm011001k

Reference yield:

: 162131-67-1
(1R,3aS,7aR)-3a-hydroxy-7a-methylperhydroindene-5-spiro-2'-(1',3'-dioxolane)-1-carboxaldehyde

: 392235-12-0
(1S,3aS,5S,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a,5-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1.4 M KOH; MeOH / 0.5 h / 20 °C

2.1: NaBH₄ / 2.5 h / -20 °C

3.1: 68 percent / 1 N pTSA / acetonitrile; H₂O / 16 h

4.1: tert-butyllithium / diethyl ether; pentane / 1.33 h / -78 - 0 °C

4.2: 61 percent / diethyl ether; pentane; tetrahydrofuran / 0.5 h / -78 °C

With methanol; potassium hydroxide; sodium tetrahydroborate; tert.-butyl lithium; toluene-4-sulfonic acid; In diethyl ether; water; acetonitrile; pentane;
DOI:10.1021/jm011001k