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

Base Information

• 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
• Mol file: 1373432-23-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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 + (3S,4S)-3-methyl-4-(triisopropylsilyloxy)pentanal (1373432-22-4) → (2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one (1373432-23-5)

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:

(2S,3S)-2-methyl-3-(triisopropylsilyloxy)butan-1-ol (1373432-39-3) → (2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one (1373432-23-5)

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:

(2S,3S)-2-methyl-3-(triisopropylsilyloxy)butyl methanesulfonate (1373432-20-2) → (2S,3R,5S,6S)-2-allyl-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-methyl-6-(triisopropylsilyloxy)heptan-1-one (1373432-23-5)

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

upstream raw materials:

(3S,4S)-3-methyl-4-(triisopropylsilyloxy)pentanal

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

(2S,3S)-2-methyl-3-(triisopropylsilyloxy)butyl methanesulfonate

(2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylbutan-1-one

Downstream raw materials:

(2R,3R,5S,6S)-2-allyl-3-(4-methoxybenzyloxy)-5-methyl-6-(triisopropylsilyloxy)heptan-1-ol

(2R,3R,5S,6S)-2-allyl-3-(4-methoxybenzyloxy)-5-methyl-6-(triisopropylsilyloxy)heptyl methanesulfonate

triisopropyl((2S,3S,5R,6S)-5-(4-methoxybenzyloxy)-3,6-dimethylnon-8-en-2-yloxy)silane

(2S,7S,8R,10S,11S,E)-2-(benzyloxy)-8-(4-methoxybenzyloxy)-7,10-dimethyl-11-(triisopropylsilyloxy)dodec-4-en-3-one