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

Base Information

Chemical Name:(1R)-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-oxocyclopentane carboxylic acid benzyl ester
CAS No.:953780-59-1
Molecular Formula:C₂₁H₂₆O₇
Molecular Weight:390.433
Hs Code.:

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

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

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

There total 1 articles about (1R)-1-[(S)-acetoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-oxocyclopentane 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: 36.0%

: 112207-03-1
benzyl 2-oxocyclopentanecarboxylate

: 108-24-7
acetic anhydride

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 2-oxocyclopentanecarboxylic acid benzyl ester

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

Guidance literature:: benzyl 2-oxocyclopentanecarboxylate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; pentane; at -78 ℃; for 2h;

2,3-isopropylidene-glyceraldehyde; In tetrahydrofuran; pentane; for 0.5h;

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

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:

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

: 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:: Multi-step reaction with 2 steps

1.1: NaBH₄ / methanol

1.2: 71 percent / pyridine / CH₂Cl₂

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

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

2.3: 70 percent / toluene / 12 h / Heating

With sodium tetrahydroborate; hydrogen; palladium on activated charcoal; In methanol; 2.2: Curtius rearrangement;
DOI:10.1016/j.carres.2007.07.003