(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one

Base Information

Chemical Name:(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one
CAS No.:950588-55-3
Molecular Formula:C₂₈H₃₇NO₃S₂Si
Molecular Weight:527.824
Hs Code.:

Synonyms:(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one

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Chemical Property of (3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one

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Technology Process of (3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one

There total 1 articles about (3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one 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%

: 101979-45-7
(S)-3-acetyl-4-isopropyl-1,3-thiazolidine-2-thione

: 131380-48-8
(E)-4-(t-butyldiphenylsilyl)oxy-2-butenal

: 950588-55-3
(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one

Guidance literature:: (S)-3-acetyl-4-isopropyl-1,3-thiazolidine-2-thione; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 2h;

(E)-4-(t-butyldiphenylsilyl)oxy-2-butenal; In dichloromethane; at -78 ℃; for 6h; Further stages.;
DOI:10.1021/ol701564x

Reference yield: 71.0%

: 950588-55-3
(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 950588-56-4
(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxyhex-4-enoic acid N-methoxy-N-methylamide

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1021/ol701564x DOI:10.1021/jo800335g

Reference yield:

: 950588-55-3
(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one

: 950588-57-5
(3R)-3-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-3-hydroxy-N-methoxy-N-methylpropionamide

Guidance literature:: Multi-step reaction with 2 steps

1: 71 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

2: 97 percent / diethylzinc / CH₂Cl₂; hexane / 3 h / -15 - 20 °C

With 1H-imidazole; diethylzinc; In hexane; dichloromethane; 2: Simmons-Smith cyclopropanation;
DOI:10.1021/ol701564x