Acetic acid (1S,4R,5S)-4,5-bis-benzyloxy-1-benzyloxymethyl-cyclopent-2-enyl ester

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Chemical Name:Acetic acid (1S,4R,5S)-4,5-bis-benzyloxy-1-benzyloxymethyl-cyclopent-2-enyl ester
CAS No.:244271-49-6
Molecular Formula:C₂₉H₃₀O₅
Molecular Weight:458.554
Hs Code.:

Synonyms:Acetic acid (1S,4R,5S)-4,5-bis-benzyloxy-1-benzyloxymethyl-cyclopent-2-enyl ester

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Chemical Property of Acetic acid (1S,4R,5S)-4,5-bis-benzyloxy-1-benzyloxymethyl-cyclopent-2-enyl ester

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Technology Process of Acetic acid (1S,4R,5S)-4,5-bis-benzyloxy-1-benzyloxymethyl-cyclopent-2-enyl ester

There total 5 articles about Acetic acid (1S,4R,5S)-4,5-bis-benzyloxy-1-benzyloxymethyl-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: 70.0%

: 108-24-7
acetic anhydride

: 244271-48-5
(1S,4R,5S)-4,5-Bis-benzyloxy-1-benzyloxymethyl-cyclopent-2-enol

: 244271-49-6
Acetic acid (1S,4R,5S)-4,5-bis-benzyloxy-1-benzyloxymethyl-cyclopent-2-enyl ester

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; at 50 ℃; for 48h;
DOI:10.1016/S0040-4039(99)01141-7

Reference yield:

: 220939-94-6
(3S,4R)-1,3,4-tris(benzyloxy)-hex-5-en-2-one

: 244271-49-6
Acetic acid (1S,4R,5S)-4,5-bis-benzyloxy-1-benzyloxymethyl-cyclopent-2-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / tetrahydrofuran / 16 h / -78 - 20 °C

2: 94 percent / 2,6-lutidine / 16 h / 20 °C

3: 90 percent / Schrock's catalyst / benzene / 16 h / 20 °C

4: 97 percent / Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 16 h / 0 - 20 °C

5: 70 percent / NEt₃; DMAP / tetrahydrofuran / 48 h / 50 °C

With 2,6-dimethylpyridine; dmap; tetrabutyl ammonium fluoride; triethylamine; bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum; In tetrahydrofuran; benzene; 1: Grignard reaction / 2: Substitution / 3: ring-closing metathesis / 4: Substitution / 5: Acetylation;
DOI:10.1016/S0040-4039(99)01141-7

Reference yield:

: 226225-94-1
(3S,4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-hepta-1,6-dien-3-ol

: 244271-49-6
Acetic acid (1S,4R,5S)-4,5-bis-benzyloxy-1-benzyloxymethyl-cyclopent-2-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / 2,6-lutidine / 16 h / 20 °C

2: 90 percent / Schrock's catalyst / benzene / 16 h / 20 °C

3: 97 percent / Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 16 h / 0 - 20 °C

4: 70 percent / NEt₃; DMAP / tetrahydrofuran / 48 h / 50 °C

With 2,6-dimethylpyridine; dmap; tetrabutyl ammonium fluoride; triethylamine; bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum; In tetrahydrofuran; benzene; 1: Substitution / 2: ring-closing metathesis / 3: Substitution / 4: Acetylation;
DOI:10.1016/S0040-4039(99)01141-7