(3aS,4R,6S,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate

Base Information

• Chemical Name: (3aS,4R,6S,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate
• CAS No.: 94324-33-1
• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.396
• Mol file: 94324-33-1.mol

Synonyms:(3aS,4R,6S,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate

Chemical Property of (3aS,4R,6S,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4R,6S,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate

There total 5 articles about (3aS,4R,6S,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate 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:

Benzoic acid (S)-2-bromo-1-[(4S,5S)-5-((Z)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester (94324-29-5) → (3aS,4R,6S,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate (94324-33-1) + (3aS,4R,6R,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate (94424-53-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00204a029

Reference yield:

Benzoic acid (S)-2-bromo-1-[(4S,5S)-5-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester (94324-30-8) → (3aS,4R,6S,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate (94324-33-1) + (3aS,4R,6R,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate (94424-53-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00204a029

Reference yield:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → (3aS,4R,6S,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate (94324-33-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Ph₃P, NBS / CH₂Cl₂

2: Dibal-H / -78 °C

3: 2.) pyridine / 1.) DME, 25 deg C

4: Bu₃SnH/AIBN / benzene / 80 °C

With pyridine; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; diisobutylaluminium hydride; triphenylphosphine; In dichloromethane; benzene;

DOI:10.1021/jo00204a029

upstream raw materials:

Benzoic acid (S)-2-bromo-1-[(4S,5S)-5-((Z)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester

Benzoic acid (S)-2-bromo-1-[(4S,5S)-5-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester

2,3-O-isopropylidene-D-ribonic-γ-lactone

(3R,4S,5S)-5-(bromomethyl)-3,4-O-isopropylidenetetrahydrofuran-2,3,4-triol