acetic acid 2-bromo-3-[3-(toluene-4-sulfonyloxy)-propyl]-cyclopent-2-enyl ester

Base Information

Chemical Name:acetic acid 2-bromo-3-[3-(toluene-4-sulfonyloxy)-propyl]-cyclopent-2-enyl ester
CAS No.:252235-51-1
Molecular Formula:C₁₇H₂₁BrO₅S
Molecular Weight:417.321
Hs Code.:

Synonyms:acetic acid 2-bromo-3-[3-(toluene-4-sulfonyloxy)-propyl]-cyclopent-2-enyl ester

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Chemical Property of acetic acid 2-bromo-3-[3-(toluene-4-sulfonyloxy)-propyl]-cyclopent-2-enyl ester

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Technology Process of acetic acid 2-bromo-3-[3-(toluene-4-sulfonyloxy)-propyl]-cyclopent-2-enyl ester

There total 6 articles about acetic acid 2-bromo-3-[3-(toluene-4-sulfonyloxy)-propyl]-cyclopent-2-enyl 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:

: 108-24-7
acetic anhydride

: Toluene-4-sulfonic acid 3-((R)-2-bromo-3-hydroxy-cyclopent-1-enyl)-propyl ester

: 252235-51-1
acetic acid 2-bromo-3-[3-(toluene-4-sulfonyloxy)-propyl]-cyclopent-2-enyl ester

: Acetic acid (S)-2-bromo-3-[3-(toluene-4-sulfonyloxy)-propyl]-cyclopent-2-enyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1.5h; Title compound not separated from byproducts;
DOI:10.1021/ja991650+

Reference yield:

: 14203-24-8
2-bromo-cyclopentane-1,3-dione

: 252235-51-1
acetic acid 2-bromo-3-[3-(toluene-4-sulfonyloxy)-propyl]-cyclopent-2-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: methyl magnesium chloride; Mg / tetrahydrofuran / 3 h / Heating

1.2: tetrahydrofuran / 0 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 18 h / -10 °C

3.1: B-methyloxazaborolidine (from L-proline); BH₃ / tetrahydrofuran / -15 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

With dmap; (R)-methyl oxazaborolidine; borane; methylmagnesium chloride; magnesium; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Grignard reaction / 1.2: Addition / 2.1: Tosylation / 3.1: enantioselective reduction / 4.1: Acetylation;
DOI:10.1021/ja991650+

Reference yield:

: 252235-49-7
Toluene-4-sulfonic acid 3-(3-oxo-cyclopent-1-enyl)-propyl ester

: 252235-51-1
acetic acid 2-bromo-3-[3-(toluene-4-sulfonyloxy)-propyl]-cyclopent-2-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 69 percent / Br₂ / CH₂Cl₂ / 4 h / 20 °C

2: B-methyloxazaborolidine (from L-proline); BH₃ / tetrahydrofuran / -15 °C

3: Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

With dmap; (R)-methyl oxazaborolidine; borane; bromine; triethylamine; In tetrahydrofuran; dichloromethane; 1: Bromination / 2: enantioselective reduction / 3: Acetylation;
DOI:10.1021/ja991650+