(2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one

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Chemical Name:(2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one
CAS No.:1373432-23-5
Molecular Formula:C₃₀H₄₉NO₃S₂Si
Molecular Weight:563.941
Hs Code.:

Synonyms:(2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one

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Chemical Property of (2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one

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Technology Process of (2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one

There total 6 articles about (2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-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: 86.0%

: 1-[(4s)-4-benzyl-2-thioxo(1,3-thiazolidin-3-yl)]pent-4-en-1-one

: 1373432-22-4
(3S,4S)-3-methyl-4-(triisopropylsilyloxy)pentanal

: 1373432-23-5
(2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one

Guidance literature:: 1-[(4s)-4-benzyl-2-thioxo(1,3-thiazolidin-3-yl)]pent-4-en-1-one; With 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃;

(3S,4S)-3-methyl-4-(triisopropylsilyloxy)pentanal; In dichloromethane; for 1h; optical yield given as %de;
DOI:10.1021/ol300785c

Reference yield:

: 1373432-39-3
(2S,3S)-2-methyl-3-(triisopropylsilyloxy)butan-1-ol

: 1373432-23-5
(2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C

2.1: tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 48 h / 60 °C

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C

4.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

4.2: 1 h

With 1-methyl-pyrrolidin-2-one; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol300785c

Reference yield:

: 1373432-20-2
(2S,3S)-2-methyl-3-(triisopropylsilyloxy)butyl methanesulfonate

: 1373432-23-5
(2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 48 h / 60 °C

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C

3.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

3.2: 1 h

With 1-methyl-pyrrolidin-2-one; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol300785c