methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

Base Information

• Chemical Name: methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate
• CAS No.: 171963-38-5
• Molecular Formula: C₈H₁₂O₅
• Molecular Weight: 188.18
• Mol file: 171963-38-5.mol

Synonyms:methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

Chemical Property of methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

There total 24 articles about methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-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: 99.0%

methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate (78844-86-7) → methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate (171963-38-5)

Guidance literature:

With trifluoroacetic acid; Ambient temperature;

DOI:10.1016/0040-4020(96)00574-1

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%

(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)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; at 18 ℃; for 12h;

DOI:10.1021/jo034689c

upstream raw materials:

methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate

diazomethane

3(S),4(S),5(R)-trihydroxy-1-cyclohexene-1-carboxylic acid

methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate

Downstream raw materials:

3(S),4(S),5(R)-trihydroxy-1-cyclohexene-1-carboxylic acid

(+)-Methyl shikimate