(2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one

Base Information

• Chemical Name: (2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one
• CAS No.: 1192034-03-9
• Molecular Formula: C₂₃H₂₇NO₃S₂
• Molecular Weight: 429.604
• Mol file: 1192034-03-9.mol

Synonyms:(2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one

Chemical Property of (2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one

There total 1 articles about (2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-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%

(R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)propan-1-one (863324-53-2) + 3-Benzyloxypropanal (19790-60-4) → (2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one (1192034-03-9)

Guidance literature:

(R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)propan-1-one; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.166667h;

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

3-Benzyloxypropanal; In 1-methyl-pyrrolidin-2-one; dichloromethane; at -78 - 0 ℃; for 3h; diastereoselective reaction;

DOI:10.1002/ejoc.201500629

Reference yield: 89.0%

(2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one (1192034-03-9) → (2S,3S)-5-(benzyloxy)-2-methylpentane-1,3-diol (503620-04-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃;

DOI:10.1002/ejoc.201500629

Reference yield:

(2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one (1192034-03-9) + t-butyldimethylsiyl triflate (69739-34-0) → C29H41NO3S2Si (1192034-05-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ja906056v

upstream raw materials:

(R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)propan-1-one

3-Benzyloxypropanal

Downstream raw materials:

C₂₉H₄₁NO₃S₂Si

(2S,3S)-5-(benzyloxy)-2-methylpentane-1,3-diol