methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate

Base Information

• Chemical Name: methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate
• CAS No.: 245054-34-6
• Molecular Formula: C₁₅H₁₆O₆
• Molecular Weight: 292.288
• Mol file: 245054-34-6.mol

Synonyms:methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate

Chemical Property of methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate

There total 16 articles about methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-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: 98.0%

(2S,3S,4aR,8S,8aR)-methyl 8-hydroxy-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate (245054-31-3) → methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate (171963-38-5) + methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate (245054-34-6)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1016/S0040-4020(99)00431-7

Reference yield: 94.0%

(1R,5R,6R)-5-Benzoyloxy-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester (275355-06-1) → methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate (245054-34-6)

Guidance literature:

With boron trifluoride diethyl etherate; In toluene; at 20 ℃;

DOI:10.1021/ol005805q

Reference yield:

vinyl benzoate (769-78-8,24991-32-0) + methyl shikimate (40983-58-2) → methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate (245054-34-6) + methyl (3R,4S,5R)-4-benzoyloxy-3,5-dihydroxy-cyclohex-1-en-1-carboxylate

Guidance literature:

With Candida antarctica Lipase A; 4 A molecular sieve; In various solvent(s); at 40 ℃; for 8h; Enzymatic reaction;

DOI:10.1021/jo025671p

upstream raw materials:

(2S,3S,4aR,8S,8aR)-methyl 8-hydroxy-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate

methyl (3R,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

(1R,5R,6R)-5-Benzoyloxy-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester

vinyl benzoate

Downstream raw materials:

shikimic acid

methyl shikimate