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

Base Information

Chemical Name:(1S,4R,5R)-5-Acetoxy-1-benzyloxycarbonyloxy-4-bromo-cyclohex-2-enecarboxylic acid methyl ester
CAS No.:183134-55-6
Molecular Formula:C₁₈H₁₉BrO₇
Molecular Weight:427.249
Hs Code.:

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

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Chemical Property of (1S,4R,5R)-5-Acetoxy-1-benzyloxycarbonyloxy-4-bromo-cyclohex-2-enecarboxylic acid methyl ester

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Technology Process of (1S,4R,5R)-5-Acetoxy-1-benzyloxycarbonyloxy-4-bromo-cyclohex-2-enecarboxylic acid methyl ester

There total 2 articles about (1S,4R,5R)-5-Acetoxy-1-benzyloxycarbonyloxy-4-bromo-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: 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:

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

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

Guidance literature:: Multi-step reaction with 2 steps

1: 48 percent / aq. TFA / 72 h

2: 91 percent / acetonitrile / 0.5 h / 0 °C

With trifluoroacetic acid; In acetonitrile;
DOI:10.1039/p19960002371

Reference yield:

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

: 183134-59-0
(1R,3S)-1,3-Dihydroxy-cyclohexanecarboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

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

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

With lithium hydroxide; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; palladium on activated charcoal; In tetrahydrofuran;
DOI:10.1039/p19960002371