(1S,4S,5R)-1-Benzyloxycarbonyloxy-4,5-dihydroxy-cyclohex-2-enecarboxylic acid methyl ester

Base Information

Chemical Name:(1S,4S,5R)-1-Benzyloxycarbonyloxy-4,5-dihydroxy-cyclohex-2-enecarboxylic acid methyl ester
CAS No.:183134-54-5
Molecular Formula:C₁₆H₁₈O₇
Molecular Weight:322.315
Hs Code.:

Synonyms:(1S,4S,5R)-1-Benzyloxycarbonyloxy-4,5-dihydroxy-cyclohex-2-enecarboxylic acid methyl ester

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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 (1S,4S,5R)-1-Benzyloxycarbonyloxy-4,5-dihydroxy-cyclohex-2-enecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (1S,4S,5R)-1-Benzyloxycarbonyloxy-4,5-dihydroxy-cyclohex-2-enecarboxylic acid methyl ester

There total 1 articles about (1S,4S,5R)-1-Benzyloxycarbonyloxy-4,5-dihydroxy-cyclohex-2-enecarboxylic acid methyl ester 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: 48.0%

: Methyl (1S,4S,5R)-1-(benzyloxycarbonyloxy)-4,5-(cyclohexylidenedioxy)cyclohex-2-ene-1-carboxylate

: 183134-54-5
(1S,4S,5R)-1-Benzyloxycarbonyloxy-4,5-dihydroxy-cyclohex-2-enecarboxylic acid methyl ester

Guidance literature:: With trifluoroacetic acid; for 72h;
DOI:10.1039/p19960002371

Reference yield: 91.0%

: 40635-67-4
acetoxyisobutyryl bromide

: 183134-54-5
(1S,4S,5R)-1-Benzyloxycarbonyloxy-4,5-dihydroxy-cyclohex-2-enecarboxylic acid methyl ester

: 183134-55-6
(1S,4R,5R)-5-Acetoxy-1-benzyloxycarbonyloxy-4-bromo-cyclohex-2-enecarboxylic acid methyl ester

Guidance literature:: In acetonitrile; at 0 ℃; for 0.5h;
DOI:10.1039/p19960002371

Reference yield:

: 183134-54-5
(1S,4S,5R)-1-Benzyloxycarbonyloxy-4,5-dihydroxy-cyclohex-2-enecarboxylic acid methyl ester

: 183134-62-5
(R)-1-Hydroxy-3-oxo-cyclohexanecarboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / acetonitrile / 0.5 h / 0 °C

2: 1.) Bu₃SnH, AIBN, 2.) H₂ / 2.) 30percent Pd/C / 1.) toluene, r.t., 2 d, 2.) EtOH, 60 deg C, 5 atm, 18 h

3: aq. LiOH / tetrahydrofuran / 0.5 h / Ambient temperature

4: 70 percent / DMAP, NEt₃, Bu₄NI / dimethylformamide / 48 h

5: 84 percent / PDC / CH₂Cl₂ / 48 h / Ambient temperature

6: 88 percent / H₂ / 5percent Pd/C / methanol / 0.5 h / Ambient temperature

With dmap; lithium hydroxide; dipyridinium dichromate; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/p19960002371