(-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

Base Information

Chemical Name:(-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene
CAS No.:875545-09-8
Molecular Formula:C₂₁H₃₂O₃Si
Molecular Weight:360.569
Hs Code.:

Synonyms:(-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

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Chemical Property of (-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

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Technology Process of (-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

There total 2 articles about (-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene 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: 100.0%

: (1R,2R,3R,5R)-2-((S)-1-Phenyl-ethoxy)-8-oxa-bicyclo[3.2.1]oct-6-en-3-ol

: 69739-34-0
t-butyldimethylsiyl triflate

: 875545-09-8
(-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/j.tet.2005.08.112

Reference yield:

: 209852-87-9
(-)-(1'S,2S)-2α-(1-Phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-3-one

: 875545-09-8
(-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / sodium borohydride / methanol / 3 h / -78 °C

2: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; In methanol; dichloromethane;
DOI:10.1016/j.tet.2005.08.112

Reference yield: 92.0%

: 875545-09-8
(-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

: 875545-10-1
[(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: (-)-(1R,2S,3R,5R)-2-((S)-1-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-ene; With ozone; In methanol; dichloromethane; at -78 ℃;

With sodium tetrahydroborate; In methanol; dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.tet.2005.08.112