(5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 220431-77-6
• Molecular Formula: C₁₀H₁₅NO₅
• Molecular Weight: 229.233
• Mol file: 220431-77-6.mol

Synonyms:(5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property of (5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl ester

There total 2 articles about (5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl 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: 41.0%

(1S,2R,3S,4R)-3-Methoxycarbonylamino-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (220431-76-5) → (5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl ester (220431-77-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -10 ℃; for 2h;

DOI:10.1055/s-1999-2539

Reference yield:

(1S,2R,3S,4R)-3-Azidocarbonyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (220431-75-4) → (5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl ester (220431-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) toluene, reflux, 3 h, 2.) toluene, reflux, 2 h

2: 41 percent / LiHDMS / tetrahydrofuran; hexane / 2 h / -10 °C

With lithium hexamethyldisilazane; In tetrahydrofuran; hexane;

DOI:10.1055/s-1999-2539

Reference yield: 87.0%

(5R,6S)-5-Hydroxy-6-methoxycarbonylamino-cyclohex-1-enecarboxylic acid methyl ester (220431-77-6) → (1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic acid methyl ester (220431-78-7)

Guidance literature:

With hydrogen; 10% palladium on active carbon; In ethanol; ethyl acetate; for 144h; under 2475.2 Torr;

DOI:10.1055/s-1999-2539

upstream raw materials:

(1S,2R,3S,4R)-3-Methoxycarbonylamino-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

(1S,2R,3S,4R)-3-Azidocarbonyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

Downstream raw materials:

(1S,2S,3R)-3-Hydroxy-2-methoxycarbonylamino-cyclohexanecarboxylic acid methyl ester