Acetic acid (1R,3S,4R,6S)-4-benzyloxycarbonylamino-7-oxa-bicyclo[4.1.0]hept-3-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (1R,3S,4R,6S)-4-benzyloxycarbonylamino-7-oxa-bicyclo[4.1.0]hept-3-ylmethyl ester
• CAS No.: 124678-08-6
• Molecular Formula: C₁₇H₂₁NO₅
• Molecular Weight: 319.357
• Mol file: 124678-08-6.mol

Synonyms:Acetic acid (1R,3S,4R,6S)-4-benzyloxycarbonylamino-7-oxa-bicyclo[4.1.0]hept-3-ylmethyl ester

Chemical Property of Acetic acid (1R,3S,4R,6S)-4-benzyloxycarbonylamino-7-oxa-bicyclo[4.1.0]hept-3-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,3S,4R,6S)-4-benzyloxycarbonylamino-7-oxa-bicyclo[4.1.0]hept-3-ylmethyl ester

There total 4 articles about Acetic acid (1R,3S,4R,6S)-4-benzyloxycarbonylamino-7-oxa-bicyclo[4.1.0]hept-3-ylmethyl 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: 95.0%

acetic anhydride (108-24-7) + ((1S,3R,4S,6R)-4-Hydroxymethyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-carbamic acid benzyl ester (124678-02-0) → Acetic acid (1R,3S,4R,6S)-4-benzyloxycarbonylamino-7-oxa-bicyclo[4.1.0]hept-3-ylmethyl ester (124678-08-6)

Guidance literature:

In dichloromethane; triethylamine; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)99612-6

Reference yield: 72.0%

Acetic acid (1R,6S)-6-benzyloxycarbonylamino-cyclohex-3-enylmethyl ester (124678-05-3) → Acetic acid (1R,3S,4R,6S)-4-benzyloxycarbonylamino-7-oxa-bicyclo[4.1.0]hept-3-ylmethyl ester (124678-08-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1016/S0040-4039(00)99612-6

Reference yield:

((1S,6R)-6-Hydroxymethyl-cyclohex-3-enyl)-carbamic acid benzyl ester (124678-01-9,213672-73-2) → Acetic acid (1R,3S,4R,6S)-4-benzyloxycarbonylamino-7-oxa-bicyclo[4.1.0]hept-3-ylmethyl ester (124678-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / triethylamine; CH₂Cl₂; various solvent(s) / 1 h / 0 °C

2: 72 percent / MCPBA / CH₂Cl₂ / 16 h / Ambient temperature

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; triethylamine;

DOI:10.1016/S0040-4039(00)99612-6

upstream raw materials:

acetic anhydride

((1S,3R,4S,6R)-4-Hydroxymethyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-carbamic acid benzyl ester

Acetic acid (1R,6S)-6-benzyloxycarbonylamino-cyclohex-3-enylmethyl ester

((1S,6R)-6-Hydroxymethyl-cyclohex-3-enyl)-carbamic acid benzyl ester