(3S,4E,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-((4S)-4-isopropyl-2-thioxothiazolidin-3-yl)-4,6-dimethylhept-4-en-1-one

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Chemical Name:(3S,4E,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-((4S)-4-isopropyl-2-thioxothiazolidin-3-yl)-4,6-dimethylhept-4-en-1-one
CAS No.:875439-62-6
Molecular Formula:C₃₁H₄₃NO₃S₂Si
Molecular Weight:569.905
Hs Code.:

Synonyms:(3S,4E,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-((4S)-4-isopropyl-2-thioxothiazolidin-3-yl)-4,6-dimethylhept-4-en-1-one

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Chemical Property of (3S,4E,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-((4S)-4-isopropyl-2-thioxothiazolidin-3-yl)-4,6-dimethylhept-4-en-1-one

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Technology Process of (3S,4E,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-((4S)-4-isopropyl-2-thioxothiazolidin-3-yl)-4,6-dimethylhept-4-en-1-one

There total 3 articles about (3S,4E,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-((4S)-4-isopropyl-2-thioxothiazolidin-3-yl)-4,6-dimethylhept-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: 83.0%

: 121929-87-1
(R)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone

: 165258-10-6
(4S,2E)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpent-2-enal

: 875439-62-6
(3S,4E,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-((4S)-4-isopropyl-2-thioxothiazolidin-3-yl)-4,6-dimethylhept-4-en-1-one

Guidance literature:: (R)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone; With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate; In dichloromethane; at -50 ℃; for 4h;

(4S,2E)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpent-2-enal; In dichloromethane; at -78 ℃;
DOI:10.1021/ol052588q

Reference yield:

: 144604-72-8
(4S,2E)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpent-2-en-1-ol

: 875439-62-6
(3S,4E,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-((4S)-4-isopropyl-2-thioxothiazolidin-3-yl)-4,6-dimethylhept-4-en-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0 °C

2.1: tin(II) triflate; N-ethyl piperidine / CH₂Cl₂ / 4 h / -50 °C

2.2: 83 percent / CH₂Cl₂ / -78 °C

With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; 2.2: aldol reaction;
DOI:10.1021/ol052588q

Reference yield:

: 142592-66-3
ethyl (2E,4S)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpent-2-enoate

: 875439-62-6
(3S,4E,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-1-((4S)-4-isopropyl-2-thioxothiazolidin-3-yl)-4,6-dimethylhept-4-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 99 percent / DIBAL-H / hexane; CH₂Cl₂ / 0.17 h / -78 °C

2.1: 93 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0 °C

3.1: tin(II) triflate; N-ethyl piperidine / CH₂Cl₂ / 4 h / -50 °C

3.2: 83 percent / CH₂Cl₂ / -78 °C

With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In hexane; dichloromethane; 3.2: aldol reaction;
DOI:10.1021/ol052588q