ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate

Base Information

Chemical Name:ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate
CAS No.:1224733-28-1
Molecular Formula:C₁₉H₂₂O₉S
Molecular Weight:426.444
Hs Code.:

Synonyms:ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate

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Technology Process of ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate

There total 5 articles about ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate 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%

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

: 124-63-0
methanesulfonyl chloride

: 1224733-28-1
ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1002/ejoc.202100653

Reference yield: 85.0%

: 1149345-82-3
ethyl (3R,4R,5R)-5-O-benzoyl-3,4-O-bis(methanesulfonyl)shikimate

: 64-19-7,77671-22-8
acetic acid

: 1224733-28-1
ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 50 ℃; for 4h; optical yield given as %ee; regioselective reaction;
DOI:10.1016/j.tetasy.2009.12.028

Reference yield:

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

: 1224733-28-1
ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 30 h / Reflux

2: triethylamine; dmap / dichloromethane / 2 h / 0 °C

With dmap; triethylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1002/ejoc.202100653