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

Base Information

• Chemical Name: Benzoic acid (S)-2-bromo-1-[(4S,5S)-5-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester
• CAS No.: 94324-30-8
• Molecular Formula: C₁₉H₂₃BrO₆
• Molecular Weight: 427.292
• Mol file: 94324-30-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about Benzoic acid (S)-2-bromo-1-[(4S,5S)-5-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl 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:

phenylglyoxylyl chloride (25726-04-9) + (3R,4S,5S)-5-(bromomethyl)-3,4-O-isopropylidenetetrahydrofuran-2,3,4-triol (138946-44-8) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → 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) + 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)

Guidance literature:

With pyridine; Multistep reaction; 1.) DME, 25 deg C;

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

upstream raw materials:

phenylglyoxylyl chloride

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

ethyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

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

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