(1S,2R,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,2R,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester
CAS No.:188307-33-7
Molecular Formula:C₂₃H₃₄O₅Si
Molecular Weight:418.605
Hs Code.:

Synonyms:(1S,2R,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester

Suppliers and Price of (1S,2R,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (1S,2R,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester

There total 5 articles about (1S,2R,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester 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%

: 69739-34-0
t-butyldimethylsiyl triflate

: 188307-32-6
(1S,2S,3R,5S)-2-Benzyloxymethyl-3-hydroxy-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester

: 188307-33-7
(1S,2R,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester

Guidance literature:: With lutidine; In dichloromethane; 0 deg C to rt;
DOI:10.1016/S0040-4039(96)02481-1

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 188307-33-7
(1S,2R,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 33 percent / NaH / dioxane / 0 deg C to rt

2: 36 percent / NaBH₄, CeCl₃ / methanol; ethanol / -78 °C

3: 94 percent / lutidine / CH₂Cl₂ / 0 deg C to rt

With sodium tetrahydroborate; cerium(III) chloride; lutidine; sodium hydride; In 1,4-dioxane; methanol; ethanol; dichloromethane;
DOI:10.1016/S0040-4039(96)02481-1

Reference yield:

: 40458-77-3
meso-8-oxabicyclo[3.2.1]oct-6-en-3-one

: 188307-33-7
(1S,2R,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / LiCl, (-)-bis<(S)-1-phenylethyl>amine, n-butyllithium / tetrahydrofuran / -94 deg C to rt

2: 33 percent / NaH / dioxane / 0 deg C to rt

3: 36 percent / NaBH₄, CeCl₃ / methanol; ethanol / -78 °C

4: 94 percent / lutidine / CH₂Cl₂ / 0 deg C to rt

With sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; (-)-bis<(S)-1-phenylethyl>amine; lutidine; sodium hydride; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane;
DOI:10.1016/S0040-4039(96)02481-1