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

Base Information

Chemical Name:(2R,3S,4S,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-(tert-butyl-dimethylsilyloxy)-5-methoxy-2,4-dimethylheptan-1-one
CAS No.:1391093-72-3
Molecular Formula:C₃₃H₄₉NO₄S₂Si
Molecular Weight:615.974
Hs Code.:

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

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

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

There total 5 articles about (2R,3S,4S,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-(tert-butyl-dimethylsilyloxy)-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: 88.0%

: 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

: 69739-34-0
t-butyldimethylsiyl triflate

: 1391093-72-3
(2R,3S,4S,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-(tert-butyl-dimethylsilyloxy)-5-methoxy-2,4-dimethylheptan-1-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1016/j.tetlet.2012.05.103

Reference yield:

: 1391093-66-5
((2R,3S)-5-(benzyloxy)-3-methoxy-2-methylpentyloxy)(tert-butyl)dimethylsilane

: 1391093-72-3
(2R,3S,4S,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-(tert-butyl-dimethylsilyloxy)-5-methoxy-2,4-dimethylheptan-1-one

Guidance literature:: Multi-step reaction with 4 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

4.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C

With 2,6-dimethylpyridine; 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:

: 73814-98-9,73814-99-0,105560-79-0,143005-16-7
(2R,3S)-5-Benzyloxy-2-methyl-pentane-1,3-diol

: 1391093-72-3
(2R,3S,4S,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-(tert-butyl-dimethylsilyloxy)-5-methoxy-2,4-dimethylheptan-1-one

Guidance literature:: Multi-step reaction with 6 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

6.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C

With 2,6-dimethylpyridine; 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