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

Base Information

Chemical Name:(2S,3R,4S,5R,6S,7S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-methoxy-2,4,6-trimethylnonan-1-one
CAS No.:1391093-76-7
Molecular Formula:C₃₆H₅₅NO₅S₂Si
Molecular Weight:674.054
Hs Code.:

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

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

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

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

There total 6 articles about (2S,3R,4S,5R,6S,7S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-methoxy-2,4,6-trimethylnonan-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:

: 1391093-75-6
(2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal

: 263764-23-4,863324-53-2
(S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione

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

: 1391093-76-7
(2S,3R,4S,5R,6S,7S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-methoxy-2,4,6-trimethylnonan-1-one

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

With (-)-sparteine; In dichloromethane; at 0 ℃; for 0.333333h;

(2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal; In dichloromethane; at 0 ℃; for 12h; optical yield given as %de; stereoselective reaction;
DOI:10.1016/j.tetlet.2012.05.103

Reference yield:

: 1391093-64-3
(2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-ol

: 1391093-76-7
(2S,3R,4S,5R,6S,7S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-methoxy-2,4,6-trimethylnonan-1-one

Guidance literature:: Multi-step reaction with 7 steps

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

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

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 3 h / 20 °C

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

4.2: 0.33 h / 0 °C

4.3: 3 h / 0 °C

5.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C

6.1: diisobutylaluminium hydride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

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

7.2: 0.33 h / 0 °C

7.3: 12 h / 0 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; 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

Reference yield:

: 1391093-61-0
(2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one

: 1391093-76-7
(2S,3R,4S,5R,6S,7S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-methoxy-2,4,6-trimethylnonan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C

2.1: diisobutylaluminium hydride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

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

3.2: 0.33 h / 0 °C

3.3: 12 h / 0 °C

With 2,6-dimethylpyridine; titanium tetrachloride; diisobutylaluminium hydride; In dichloromethane;
DOI:10.1016/j.tetlet.2012.05.103