(1R,2R,3S)-3-Benzyloxymethoxy-5-oxo-2-vinyl-cyclopentanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1R,2R,3S)-3-Benzyloxymethoxy-5-oxo-2-vinyl-cyclopentanecarboxylic acid methyl ester
• CAS No.: 185114-38-9
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343

Synonyms:(1R,2R,3S)-3-Benzyloxymethoxy-5-oxo-2-vinyl-cyclopentanecarboxylic acid methyl ester

Chemical Property of (1R,2R,3S)-3-Benzyloxymethoxy-5-oxo-2-vinyl-cyclopentanecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (1R,2R,3S)-3-Benzyloxymethoxy-5-oxo-2-vinyl-cyclopentanecarboxylic acid methyl ester

There total 2 articles about (1R,2R,3S)-3-Benzyloxymethoxy-5-oxo-2-vinyl-cyclopentanecarboxylic 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: 71.0%

vinyl magnesium bromide (1826-67-1) + (E)-(S)-4-Benzyloxymethoxy-hex-2-enedioic acid dimethyl ester (185114-35-6) → (1R,2R,3S)-3-Benzyloxymethoxy-5-oxo-2-vinyl-cyclopentanecarboxylic acid methyl ester (185114-38-9)

Guidance literature:

With copper(l) iodide; at -30 ℃;

DOI:10.1016/S0040-4039(97)10211-8

Reference yield:

(S)-3-Benzyloxymethoxy-4-oxo-butyric acid methyl ester → (1R,2R,3S)-3-Benzyloxymethoxy-5-oxo-2-vinyl-cyclopentanecarboxylic acid methyl ester (185114-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent

2: 71 percent / CuI / -30 °C

With copper(l) iodide;

DOI:10.1016/S0040-4039(97)10211-8

Reference yield: 89.0%

(1R,2R,3S)-3-Benzyloxymethoxy-5-oxo-2-vinyl-cyclopentanecarboxylic acid methyl ester (185114-38-9) → (1R,2R,3S,5S)-3-Benzyloxymethoxy-5-hydroxy-2-vinyl-cyclopentanecarboxylic acid methyl ester

Guidance literature:

With zinc(II) tetrahydroborate;

DOI:10.1016/S0040-4039(97)10211-8

upstream raw materials:

vinyl magnesium bromide

(E)-(S)-4-Benzyloxymethoxy-hex-2-enedioic acid dimethyl ester

Downstream raw materials:

[(1S,2R,3R,4S)-4-Benzyloxymethoxy-2-iodomethyl-3-((Z)-oct-2-enyl)-cyclopentyloxy]-tert-butyl-dimethyl-silane

4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentylmethyl ester

4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester

(Z)-(S)-7-[(1R,2R,3S,5S)-3-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-((Z)-oct-2-enyl)-cyclopentyl]-4-(tert-butyl-dimethyl-silanyloxy)-hept-5-enoic acid

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