(3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

Base Information

Chemical Name:(3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester
CAS No.:704910-39-4
Molecular Formula:C₂₆H₃₇NO₆Si
Molecular Weight:487.668
Hs Code.:

(3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

Synonyms:(3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

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Chemical Property of (3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

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Technology Process of (3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

There total 5 articles about (3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl 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: 83.0%

: 704910-45-2
3-cyclohexenyl zinc chloride

: 704910-38-3
(3S,3aS,7aR)-3-Formyl-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

: 704910-39-4
(3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

Guidance literature:: 3-cyclohexenyl zinc chloride; (3S,3aS,7aR)-3-Formyl-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester; In tetrahydrofuran; at -78 ℃; for 5h;

With water; In tetrahydrofuran;

Reference yield: 83.0%

: 704910-45-2
3-cyclohexenyl zinc chloride

: 704910-38-3
(3S,3aS,7aR)-3-Formyl-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

: (3R,3aS,7aR)-3-((R)-(R)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

: 704910-39-4
(3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 5h;
DOI:10.1021/ja048613p

Reference yield:

: methyl (2R)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde

: 704910-39-4
(3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 89 percent / tributyltin hydride; AIBN / benzene / 4 h / 80 °C

3: H₂ / Pd/C / ethanol / 12 h / 23 °C / 760 Torr

4: 2.68 g / Dess-Martin reagent / CH₂Cl₂ / 1 h / 23 °C

5: 83 percent / tetrahydrofuran / 5 h / -78 °C

With dmap; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; benzene; 4: Dess-Martin oxidation;
DOI:10.1021/ja048613p