(3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)oct-7-en-1-one

Base Information

Chemical Name:(3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)oct-7-en-1-one
CAS No.:1395342-44-5
Molecular Formula:C₂₆H₄₁NO₃S₂Si
Molecular Weight:507.834
Hs Code.:

Synonyms:(3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)oct-7-en-1-one

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Chemical Property of (3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)oct-7-en-1-one

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Technology Process of (3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)oct-7-en-1-one

There total 3 articles about (3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)oct-7-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: 88.0%

: 924265-91-8
(S)-1-(4-mesityl-2-thioxothiazolidin-3-yl)ethanone

: 1275506-53-0
(R)-3-((tert-butyldimethylsilyl)oxy)hex-5-enal

: 1395342-44-5
(3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)oct-7-en-1-one

Guidance literature:: (S)-1-(4-mesityl-2-thioxothiazolidin-3-yl)ethanone; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

(R)-3-((tert-butyldimethylsilyl)oxy)hex-5-enal; In dichloromethane; at -78 ℃; for 1h; stereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0031-1290670

Reference yield:

: 1246920-52-4
(R)-3-hydroxyl-1-((R)-4-mesityl-2-thioxothiazolidin-3-yl)hex-5-en-1-one

: 1395342-44-5
(3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)oct-7-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / -78 - 0 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

3.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; titanium tetrachloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane;
DOI:10.1055/s-0031-1290670

Reference yield:

: 1395342-26-3
(R)-3-((tert-butyldimethylsilyl)oxy)-1-((R)-4-mesityl-2-thioxothiazolidin-3-yl)hex-5-en-1-one

: 1395342-44-5
(3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)oct-7-en-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

2.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

With titanium tetrachloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane;
DOI:10.1055/s-0031-1290670