(4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(R)-ethan-1-ol

Base Information

Chemical Name:(4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(R)-ethan-1-ol
CAS No.:911371-53-4
Molecular Formula:C₂₅H₃₄O₄Si
Molecular Weight:426.628
Hs Code.:

Synonyms:(4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(R)-ethan-1-ol

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Chemical Property of (4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(R)-ethan-1-ol

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Technology Process of (4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(R)-ethan-1-ol

There total 5 articles about (4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(R)-ethan-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: 90.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

: 911371-53-4
(4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(R)-ethan-1-ol

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h;

(3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/ol061444o

Reference yield:

: 1311161-37-1
(4R,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)ethan-1-one

: 911371-53-4
(4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(R)-ethan-1-ol

: 1311161-40-6
(4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(S)-ethan-1-ol

Guidance literature:: With lithium tri-t-butoxyaluminum hydride; In ethanol; at -78 ℃; for 2h; optical yield given as %de;
DOI:10.1016/j.tetlet.2011.04.015

Reference yield:

: 1311161-38-2
C₉H₁₄O₄

: 911371-53-4
(4S,5R)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldiphenylsilyloxy)-1(R)-ethan-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 1H-imidazole / dichloromethane / 20 °C

2: lithium tri-t-butoxyaluminum hydride / ethanol / 2 h / -78 °C

With 1H-imidazole; lithium tri-t-butoxyaluminum hydride; In ethanol; dichloromethane;
DOI:10.1016/j.tetlet.2011.04.015