(2R,3S,8S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-one

Base Information

Chemical Name:(2R,3S,8S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-one
CAS No.:1420766-36-4
Molecular Formula:C₄₃H₆₃NO₃S₂Si₂
Molecular Weight:762.281
Hs Code.:

Synonyms:(2R,3S,8S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-one

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Chemical Property of (2R,3S,8S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-one

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Technology Process of (2R,3S,8S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-one

There total 7 articles about (2R,3S,8S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-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: 82.0%

: 1420766-33-1
(2R,3S,8S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-9-(tert-butyldiphenylsilyloxy)-3-hydroxy-2,8-dimethylnonan-1-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 1420766-36-4
(2R,3S,8S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.166667h;
DOI:10.1016/j.tet.2012.11.075

Reference yield:

: 1420766-28-4
C₂₄H₃₄O₂Si

: 1420766-36-4
(2R,3S,8S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-one

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 2 h / -78 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C

With 2,6-dimethylpyridine; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.2: |Evans Aldol Reaction;
DOI:10.1016/j.tet.2012.11.075

Reference yield:

: 161512-73-8
(2S)-2,6-dimethyl-5-hepten-1-ol

: 1420766-36-4
(2R,3S,8S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole / dichloromethane / 0.25 h / 0 °C

1.2: 2 h / 20 °C

2.1: ozone / dichloromethane / 0.25 h / -78 °C

2.2: 0.17 h / Reflux

3.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate; hydrogen / methanol / 4 h / 0 - 20 °C

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C

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

5.2: 2 h / -78 °C / Inert atmosphere

6.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; nickel(II) chloride hexahydrate; hydrogen; titanium tetrachloride; diisobutylaluminium hydride; ozone; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; toluene; 2.2: |Wittig Olefination / 5.2: |Evans Aldol Reaction;
DOI:10.1016/j.tet.2012.11.075