7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylicacid,methylester,(1S,2S,4S)-

Base Information

• Chemical Name: 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylicacid,methylester,(1S,2S,4S)-
• CAS No.: 186766-46-1
• Molecular Formula: C8H10 O3
• Molecular Weight: 154.166
• Mol file: 186766-46-1.mol

Synonyms:7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylicacid, methyl ester, (1S-endo)-

Chemical Property of 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylicacid,methylester,(1S,2S,4S)-

Chemical Property:

• PSA: 35.53000
• LogP: 0.50290

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-carboxylicacid,methylester,(1S,2S,4S)-

There total 4 articles about 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylicacid,methylester,(1S,2S,4S)- 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: 93.0%

methanol (67-56-1) + (1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carbothioic acid S-ethyl ester (245680-45-9) → (1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (186766-46-1,204988-60-3)

Guidance literature:

With caesium carbonate; at 0 ℃;

DOI:10.1021/ja991191c

Reference yield: 68.0%

furan (110-00-9) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (1S,2R,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (204988-60-3) + (1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (186766-46-1,204988-60-3)

Guidance literature:

With boron trifluoride diethyl etherate; In ethyl acetate; at -20 - 5 ℃; for 10h; Inert atmosphere;

Reference yield:

3-((1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one (186666-50-2) → (1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (186766-46-1,204988-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / -20 °C

2: 93 percent / Cs₂CO₃ / 0 °C

With caesium carbonate; In tetrahydrofuran; 1: transesterification / 2: transesterification;

DOI:10.1021/ja991191c

upstream raw materials:

(1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carbothioic acid S-ethyl ester

methanol

furan

acrylic acid methyl ester

Downstream raw materials:

(3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

(+)-Methyl shikimate

(+)-shikimic acid

furan