(1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentane carboxylic acid benzyl ester

Base Information

Chemical Name:(1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentane carboxylic acid benzyl ester
CAS No.:953780-61-5
Molecular Formula:C₂₃H₃₀O₈
Molecular Weight:434.486
Hs Code.:

Synonyms:(1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentane carboxylic acid benzyl ester

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Chemical Property of (1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentane carboxylic acid benzyl ester

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Technology Process of (1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentane carboxylic acid benzyl ester

There total 1 articles about (1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentane carboxylic acid benzyl 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%

: 953780-59-1
(1R)-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-oxocyclopentane carboxylic acid benzyl ester

: 108-24-7
acetic anhydride

: 953780-61-5
(1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentane carboxylic acid benzyl ester

Guidance literature:: (1R)-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-oxocyclopentane carboxylic acid benzyl ester; With sodium tetrahydroborate; In methanol;

acetic anhydride; With pyridine; In dichloromethane; Further stages.;
DOI:10.1016/j.carres.2007.07.003

Reference yield: 70.0%

: 953780-61-5
(1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentane carboxylic acid benzyl ester

: 100-51-6,185532-71-2
benzyl alcohol

: 953780-63-7
[(1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentyl]carbamic acid benzyl ester

Guidance literature:: (1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentane carboxylic acid benzyl ester; With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 10h;

With diphenyl-phosphinic acid; triethylamine; In toluene; for 2h; Heating;

benzyl alcohol; In toluene; for 12h; Further stages.; Heating;
DOI:10.1016/j.carres.2007.07.003

Reference yield:

: 953780-61-5
(1S,2R)-2-acetoxy-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]cyclopentane carboxylic acid benzyl ester

: 953780-64-8
[(1S,2R)-2-acetoxy-1-[(1S,2R)-1-acetoxy-2,3-dihydroxypropyl]cyclopentyl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: H₂ / Pd/C / methanol / 10 h / 20 °C

1.2: DPPA; Et₃N / toluene / 2 h / Heating

1.3: 70 percent / toluene / 12 h / Heating

2.1: 77 percent / aq. AcOH / 0.17 h / Heating

With hydrogen; acetic acid; palladium on activated charcoal; In methanol; 1.2: Curtius rearrangement;
DOI:10.1016/j.carres.2007.07.003