(3R,6S,Z)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-hydroxydec-4-en-1-one

Base Information

Chemical Name:(3R,6S,Z)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-hydroxydec-4-en-1-one
CAS No.:1329675-13-9
Molecular Formula:C₃₆H₄₅NO₃S₂Si
Molecular Weight:631.976
Hs Code.:

Synonyms:(3R,6S,Z)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-hydroxydec-4-en-1-one

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Chemical Property of (3R,6S,Z)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-hydroxydec-4-en-1-one

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Technology Process of (3R,6S,Z)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-hydroxydec-4-en-1-one

There total 5 articles about (3R,6S,Z)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-hydroxydec-4-en-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: 66.0%

: 1329675-12-8
(2S,4Z)-4-{[(tert-butyl)diphenylsilyl]oxy}oct-2-enal

: 790661-41-5
(S)-1-(4-benzyl-2-thioxothiazolidin-3-yl)ethan-1-one

: 1329675-13-9
(3R,6S,Z)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-hydroxydec-4-en-1-one

: 1329675-16-2
C₃₆H₄₅NO₃S₂Si

Guidance literature:: (S)-1-(4-benzyl-2-thioxothiazolidin-3-yl)ethan-1-one; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.416667h;

(2S,4Z)-4-{[(tert-butyl)diphenylsilyl]oxy}oct-2-enal; In dichloromethane; at 0 ℃; for 1h; optical yield given as %de; diastereoselective reaction;
DOI:10.1002/ejoc.201100510

Reference yield:

: 1329675-10-6
(4S)-4-(tert-butyldiphenylsilyloxy)oct-2-yn-1-ol

: 1329675-13-9
(3R,6S,Z)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-hydroxydec-4-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 5 h / 20 °C

2.1: hydrogen / dichloromethane / 10 h

3.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.42 h / 0 °C

3.2: 1 h / 0 °C

With hydrogen; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; 3.1: Crimmins aldol reaction / 3.2: Crimmins aldol reaction;
DOI:10.1002/ejoc.201100510

Reference yield:

: 1329675-08-2
(4S)-1-(tetrahydro-2H-pyran-2-yloxy)oct-2-yn-4-ol

: 1329675-13-9
(3R,6S,Z)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-hydroxydec-4-en-1-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole / dichloromethane / 4 h

2.1: pyridinium p-toluenesulfonate / methanol / 5 h

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 5 h / 20 °C

4.1: hydrogen / dichloromethane / 10 h

5.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.42 h / 0 °C

5.2: 1 h / 0 °C

With 1H-imidazole; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; dichloromethane; dimethyl sulfoxide; 5.1: Crimmins aldol reaction / 5.2: Crimmins aldol reaction;
DOI:10.1002/ejoc.201100510