ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate

Base Information

• Chemical Name: ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate
• CAS No.: 1149345-83-4
• Molecular Formula: C₁₇H₁₉N₃O₇S
• Molecular Weight: 409.42
• Mol file: 1149345-83-4.mol

Synonyms:ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate

Chemical Property of ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate

There total 5 articles about ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate 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: 96.0%

ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-hydroxy-cyclohex-1-ene-1-carboxylate (1350928-99-2) + methanesulfonyl chloride (124-63-0) → ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate (1149345-83-4)

Guidance literature:

With dmap; triethylamine; In ethyl acetate; at 0 ℃; for 1.25h;

DOI:10.1016/j.tetasy.2011.09.014

Reference yield: 95.0%

ethyl (3R,4R,5R)-5-O-benzoyl-3,4-O-bis(methanesulfonyl)shikimate (1149345-82-3) → ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate (1149345-83-4)

Guidance literature:

With sodium azide; In water; N,N-dimethyl-formamide; at -5 - 0 ℃; for 1.5h; regioselective reaction;

DOI:10.1016/j.tetasy.2008.11.027

Reference yield:

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester (101769-63-5) → ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate (1149345-83-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: thionyl chloride; triethylamine / dichloromethane; ethyl acetate / 14 h / 0 - 20 °C

2.1: dmap; triethylamine / dichloromethane / 0 °C

2.2: 5 h / 0 - 20 °C

3.1: sodium azide; water / N,N-dimethyl-formamide / 24 h / 20 °C

4.1: dmap; triethylamine / ethyl acetate / 1.25 h / 0 °C

With dmap; thionyl chloride; sodium azide; water; triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2011.09.014

upstream raw materials:

ethyl (3R,4R,5R)-5-O-benzoyl-3,4-O-bis(methanesulfonyl)shikimate

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester

ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-hydroxy-cyclohex-1-ene-1-carboxylate

methanesulfonyl chloride

Downstream raw materials:

ethyl (1S,5R,6S)-5-benzoyloxy-7-aza-bicyclo[4,1,0]hept-2-ene-3-carboxylate