(2S,3R,6R)-2-{3-(benzyloxy)propyl}-6-(tert-butyldiphenylsilyloxy)-3,7-dimethyloct-7-ene-1,3-diol

Base Information

Chemical Name:(2S,3R,6R)-2-{3-(benzyloxy)propyl}-6-(tert-butyldiphenylsilyloxy)-3,7-dimethyloct-7-ene-1,3-diol
CAS No.:440333-58-4
Molecular Formula:C₃₆H₅₀O₄Si
Molecular Weight:574.876
Hs Code.:

Synonyms:(2S,3R,6R)-2-{3-(benzyloxy)propyl}-6-(tert-butyldiphenylsilyloxy)-3,7-dimethyloct-7-ene-1,3-diol

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Chemical Property of (2S,3R,6R)-2-{3-(benzyloxy)propyl}-6-(tert-butyldiphenylsilyloxy)-3,7-dimethyloct-7-ene-1,3-diol

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Technology Process of (2S,3R,6R)-2-{3-(benzyloxy)propyl}-6-(tert-butyldiphenylsilyloxy)-3,7-dimethyloct-7-ene-1,3-diol

There total 5 articles about (2S,3R,6R)-2-{3-(benzyloxy)propyl}-6-(tert-butyldiphenylsilyloxy)-3,7-dimethyloct-7-ene-1,3-diol 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: 94.0%

: 440333-17-5
(2R,3R,6R)-6-(tert-butyldiphenylsilanyloxy)-2,3-epoxy-3,7-dimethyloct-7-en-1-ol

: 183312-54-1
3-benzyloxypropylmagnesium bromide

: 440333-58-4
(2S,3R,6R)-2-{3-(benzyloxy)propyl}-6-(tert-butyldiphenylsilyloxy)-3,7-dimethyloct-7-ene-1,3-diol

Guidance literature:: 3-benzyloxypropylmagnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

(2R,3R,6R)-6-(tert-butyldiphenylsilanyloxy)-2,3-epoxy-3,7-dimethyloct-7-en-1-ol; In tetrahydrofuran; at -78 - 20 ℃; for 3h; regioselective reaction; Inert atmosphere;
DOI:10.1039/c1cc16468f

Reference yield:

: C₃₂H₅₀O₂Si₂

: 440333-58-4
(2S,3R,6R)-2-{3-(benzyloxy)propyl}-6-(tert-butyldiphenylsilyloxy)-3,7-dimethyloct-7-ene-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridinium p-toluenesulfonate / methanol / 9 h / 20 °C

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane / 1 h / -20 °C / Molecular sieve

3.1: copper(l) iodide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; diethyl (2S,3S)-tartrate; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; dichloromethane; 2.1: Sharpless asymmetric epoxidation;
DOI:10.1039/c1cc16468f

Reference yield:

: 440333-44-8
(E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-octa-2,7-dien-1-ol

: 440333-58-4
(2S,3R,6R)-2-{3-(benzyloxy)propyl}-6-(tert-butyldiphenylsilyloxy)-3,7-dimethyloct-7-ene-1,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane / 1 h / -20 °C / Molecular sieve

2.1: copper(l) iodide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; diethyl (2S,3S)-tartrate; In tetrahydrofuran; dichloromethane; 1.1: Sharpless asymmetric epoxidation;
DOI:10.1039/c1cc16468f