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

Base Information

• Chemical Name: (2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-methylbutan-1-one
• CAS No.: 1415934-59-6
• Molecular Formula: C₃₁H₃₇NO₃S₂Si
• Molecular Weight: 563.857
• Mol file: 1415934-59-6.mol

Synonyms:(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-methylbutan-1-one

Chemical Property of (2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-methylbutan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-methylbutan-1-one

There total 1 articles about (2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-methylbutan-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: 56.0%

(tert-butyldiphenylsilanyloxy)acetaldehyde (115869-43-7) + (S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione (263764-23-4,863324-53-2) → (2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-methylbutan-1-one (1415934-59-6)

Guidance literature:

(S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; dichloromethane; at 0 ℃; for 0.916667h; Inert atmosphere;

(tert-butyldiphenylsilanyloxy)acetaldehyde; In 1-methyl-pyrrolidin-2-one; dichloromethane; at -78 - 0 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol3030692

Reference yield: 79.0%

(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-methylbutan-1-one (1415934-59-6) → (2R,3S)-<(tert-butyldiphenylsilyl)oxy>-2-methyl-1,3-butanediol (128329-22-6)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol3030692

Reference yield:

(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-methylbutan-1-one (1415934-59-6) → (2R,3S)-4-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2-methylbutan-1-ol (1331882-90-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 3 h / 20 °C / Inert atmosphere

2: 10-camphorsufonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

3: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; 10-camphorsufonic acid; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/ol3030692

upstream raw materials:

(tert-butyldiphenylsilanyloxy)acetaldehyde

(S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione

Downstream raw materials:

(2R,3S)-4-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2-methylbutan-1-ol

(4S,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol

(4R,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol

(2R,3S)-<(tert-butyldiphenylsilyl)oxy>-2-methyl-1,3-butanediol