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

Base Information

• Chemical Name: (1S,2R,5S)-2-Benzyloxymethyl-3-oxo-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester
• CAS No.: 188307-36-0
• Molecular Formula: C₁₇H₁₈O₅
• Molecular Weight: 302.327

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

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

Chemical Property:

Purity/Quality:

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

There total 2 articles about (1S,2R,5S)-2-Benzyloxymethyl-3-oxo-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: 33.0%

Benzyloxymethyl chloride (3587-60-8) + (1S,5S)-3-Oxo-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester → (1S,2R,5S)-2-Benzyloxymethyl-3-oxo-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester (188307-36-0)

Guidance literature:

With sodium hydride; In 1,4-dioxane; 0 deg C to rt;

DOI:10.1016/S0040-4039(96)02481-1

Reference yield:

meso-8-oxabicyclo[3.2.1]oct-6-en-3-one (40458-77-3) → (1S,2R,5S)-2-Benzyloxymethyl-3-oxo-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester (188307-36-0)

Guidance literature:

Multi-step reaction with 2 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

With n-butyllithium; (-)-bis<(S)-1-phenylethyl>amine; sodium hydride; lithium chloride; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0040-4039(96)02481-1

Reference yield: 32.0%

(1S,2R,5S)-2-Benzyloxymethyl-3-oxo-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester (188307-36-0) → (1S,2S,3R,5S)-2-Benzyloxymethyl-3-hydroxy-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester (188307-32-6) + (1S,2S,3S,5S)-2-Benzyloxymethyl-3-hydroxy-8-oxa-bicyclo[3.2.1]oct-6-ene-2-carboxylic acid methyl ester

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; ethanol; at -78 ℃;

DOI:10.1016/S0040-4039(96)02481-1

upstream raw materials:

Benzyloxymethyl chloride

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

Downstream raw materials:

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

(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

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