(2S,3S,8S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-ol

Base Information

Chemical Name:(2S,3S,8S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-ol
CAS No.:1420766-39-7
Molecular Formula:C₃₃H₅₆O₃Si₂
Molecular Weight:556.977
Hs Code.:

Synonyms:(2S,3S,8S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-ol

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Chemical Property of (2S,3S,8S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-ol

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Technology Process of (2S,3S,8S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-ol

There total 8 articles about (2S,3S,8S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-ol 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: 74.0%

: 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

: 1420766-39-7
(2S,3S,8S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-ol

Guidance literature:: With lithium borohydride; In methanol; at 0 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.tet.2012.11.075

Reference yield:

: 1420766-28-4
C₂₄H₃₄O₂Si

: 1420766-39-7
(2S,3S,8S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-ol

Guidance literature:: Multi-step reaction with 3 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

3.1: lithium borohydride / methanol / 0.5 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium borohydride; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In methanol; 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

: 1420766-39-7
(2S,3S,8S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,8-dimethylnonan-1-ol

Guidance literature:: Multi-step reaction with 7 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

7.1: lithium borohydride / methanol / 0.5 h / 0 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; lithium borohydride; 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