7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, mono(phenylmethyl) ester, (1S,2R,3S,4R)-

Base Information

• Chemical Name: 7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, mono(phenylmethyl) ester, (1S,2R,3S,4R)-
• CAS No.: 648433-02-7
• Molecular Formula: C15H14O5
• Molecular Weight: 274.273

Synonyms:(1S,2R,3S,4R)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monobenzyl ester;

Chemical Property of 7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, mono(phenylmethyl) ester, (1S,2R,3S,4R)-

Chemical Property:

• PSA: 72.83000
• LogP: 1.38400

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, mono(phenylmethyl) ester, (1S,2R,3S,4R)-

There total 2 articles about 7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, mono(phenylmethyl) ester, (1S,2R,3S,4R)- 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: 89.0%

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) + benzyl alcohol (100-51-6,185532-71-2) → (2S,3R)-3-exo-benzyloxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (648433-02-7)

Guidance literature:

With quinindine; In toluene; at -55 ℃; for 96h; enantioselective reaction; Inert atmosphere;

DOI:10.15227/orgsyn.082.0120

Reference yield:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) + benzyl alcohol (100-51-6,185532-71-2) → (2R,3S)-3-exo-benzyloxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (648433-21-0) + (2S,3R)-3-exo-benzyloxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (648433-02-7)

Guidance literature:

With Quinine; In tetrachloromethane; toluene; at -55 ℃; for 60h; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(03)00579-2

Reference yield:

chloroformic acid ethyl ester (541-41-3) + (2S,3R)-3-exo-benzyloxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (648433-02-7) → (1S,2R,3S,4R)-3-Ethoxycarbonyloxycarbonyl-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid benzyl ester

Guidance literature:

With triethylamine; In tetrahydrofuran; at -30 - -10 ℃;

DOI:10.1021/jo048389m

upstream raw materials:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

benzyl alcohol

Downstream raw materials:

(1S,2S,3S,4R)-3-[Benzyl-((R)-1-benzylcarbamoyl-3-methyl-butyl)-amino]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

C₁₆H₁₆O₅

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