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

Base Information

• Chemical Name: ethyl (3R,4R,5R)-5-O-benzoyl-3,4-O-bis(methanesulfonyl)shikimate
• CAS No.: 1149345-82-3
• Molecular Formula: C₁₈H₂₂O₁₀S₂
• Molecular Weight: 462.499
• Mol file: 1149345-82-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about ethyl (3R,4R,5R)-5-O-benzoyl-3,4-O-bis(methanesulfonyl)shikimate 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: 97.0%

ethyl (3R,4R,5R)-5-O-benzoyl-shikimate (1149345-81-2) + methanesulfonyl chloride (124-63-0) → ethyl (3R,4R,5R)-5-O-benzoyl-3,4-O-bis(methanesulfonyl)shikimate (1149345-82-3)

Guidance literature:

With dmap; triethylamine; In ethyl acetate; at 0 ℃; for 1h;

DOI:10.1016/j.tetasy.2008.11.027

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: 89.0%

ethyl (3R,4R,5R)-5-O-benzoyl-3,4-O-bis(methanesulfonyl)shikimate (1149345-82-3) + benzoic acid (65-85-0,8013-63-6) → ethyl (3S,4S,5R)-3,5-dibenzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate (1224733-30-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 50 ℃; for 6h; optical yield given as %ee; regioselective reaction;

DOI:10.1016/j.tetasy.2009.12.028

upstream raw materials:

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

methanesulfonyl chloride

Downstream raw materials:

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

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

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