(2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one

Base Information

• Chemical Name: (2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one
• CAS No.: 1391093-61-0
• Molecular Formula: C₂₇H₃₅NO₄S₂
• Molecular Weight: 501.711

Synonyms:(2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one

Chemical Property of (2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one

There total 4 articles about (2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-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: 70.0%

(2S,3S)-5-(benzyloxy)-3-methoxy-2-methylpentanal (1289377-50-9) + (S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione (263764-23-4,863324-53-2) → (2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one (1391093-61-0)

Guidance literature:

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

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.333333h;

(2S,3S)-5-(benzyloxy)-3-methoxy-2-methylpentanal; In dichloromethane; at 0 ℃; for 3h; optical yield given as %de; stereoselective reaction;

DOI:10.1016/j.tetlet.2012.05.103

Reference yield:

((2R,3S)-5-(benzyloxy)-3-methoxy-2-methylpentyloxy)(tert-butyl)dimethylsilane (1391093-66-5) → (2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one (1391093-61-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 3 h / 20 °C

3.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C

3.2: 0.33 h / 0 °C

3.3: 3 h / 0 °C

With tetrabutyl ammonium fluoride; titanium tetrachloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.tetlet.2012.05.103

Reference yield:

(2R,3S)-5-Benzyloxy-2-methyl-pentane-1,3-diol (73814-98-9,73814-99-0,105560-79-0,143005-16-7) → (2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one (1391093-61-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 6 h / 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 3 h / 20 °C

5.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C

5.2: 0.33 h / 0 °C

5.3: 3 h / 0 °C

With dmap; tetrabutyl ammonium fluoride; titanium tetrachloride; sodium hydride; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; mineral oil;

DOI:10.1016/j.tetlet.2012.05.103

upstream raw materials:

(2S,3S)-5-(benzyloxy)-3-methoxy-2-methylpentanal

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

((2R,3S)-5-(benzyloxy)-3-methoxy-2-methylpentyloxy)(tert-butyl)dimethylsilane

(2R,3S)-5-(benzyloxy)-3-methoxy-2-methylpentan-1-ol

Downstream raw materials:

(2S,3R,4S,5S,6S,7S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-7-methoxy-3-(methoxymethoxy)-2,4,6-trimethylnonan-1-one

(2S,3R,4S,5S,6S,7S)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-7-methoxy-3-(methoxymethoxy)-2,4,6-trimethylnonanal

(5S,6S,7S)-7-((2S,3S)-5-(benzyloxy)-3-methoxypentan-2-yl)-6,9,9,10,10-pentamethyl-5-((R)-pent-3-en-2-yl)-2,4,8-trioxa-9-silaundecane

(2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal

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