(2S,3R,4S,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-ol

Base Information

Chemical Name:(2S,3R,4S,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-ol
CAS No.:899798-79-9
Molecular Formula:C₂₉H₅₆O₄Si₂
Molecular Weight:524.932
Hs Code.:

Synonyms:(2S,3R,4S,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-ol

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Chemical Property of (2S,3R,4S,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-ol

Chemical Property:

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Technology Process of (2S,3R,4S,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-ol

There total 14 articles about (2S,3R,4S,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-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:

: 899798-78-8
(3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one

: 899798-79-9
(2S,3R,4S,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-ol

: (2R,3R,4S,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-ol

Guidance literature:: With tri-n-butyl-tin hydride; dimethylaluminum chloride; In hexane; dichloromethane; at -90 ℃; for 1h;
DOI:10.1021/ol060669w

Reference yield:

: 872369-17-0
(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

: 899798-79-9
(2S,3R,4S,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: nBu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / -5 °C

1.2: 3.98 g / CH₂Cl₂ / 16 h / -78 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 1 h / Heating

3.1: lithium hydroxide monohydrate; hydrogen peroxide / tetrahydrofuran; H₂O / 36 h / 20 °C

4.1: 1,1'-carbonyldiimidazole / CH₂Cl₂ / 0.5 h / 0 °C

4.2: 2.07 g / CH₂Cl₂ / 16 h / 20 °C

5.1: 78 percent / tetrahydrofuran; diethyl ether / 1.25 h / -20 - 0 °C

6.1: 1.16 g / dimethylaluminum chloride; tributyltin hydride / CH₂Cl₂; hexane / 1 h / -90 °C

With 2,6-dimethylpyridine; lithium hydroxide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; tri-n-butyl-tin hydride; dimethylaluminum chloride; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;
DOI:10.1021/ol060669w

Reference yield:

: 899798-76-6
(2S,3R,4R,5S)-7-Benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid

: 899798-79-9
(2S,3R,4S,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1,1'-carbonyldiimidazole / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 2.07 g / CH₂Cl₂ / 16 h / 20 °C

2.1: 78 percent / tetrahydrofuran; diethyl ether / 1.25 h / -20 - 0 °C

3.1: 1.16 g / dimethylaluminum chloride; tributyltin hydride / CH₂Cl₂; hexane / 1 h / -90 °C

With tri-n-butyl-tin hydride; dimethylaluminum chloride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ol060669w