(1R,4R,5S,6S)-1-Bromo-4,5,6-trihydroxy-cyclohex-2-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (1R,4R,5S,6S)-1-Bromo-4,5,6-trihydroxy-cyclohex-2-enecarboxylic acid methyl ester
• CAS No.: 134593-85-4
• Molecular Formula: C₈H₁₁BrO₅
• Molecular Weight: 267.076

Synonyms:(1R,4R,5S,6S)-1-Bromo-4,5,6-trihydroxy-cyclohex-2-enecarboxylic acid methyl ester

Chemical Property of (1R,4R,5S,6S)-1-Bromo-4,5,6-trihydroxy-cyclohex-2-enecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (1R,4R,5S,6S)-1-Bromo-4,5,6-trihydroxy-cyclohex-2-enecarboxylic acid methyl ester

There total 2 articles about (1R,4R,5S,6S)-1-Bromo-4,5,6-trihydroxy-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: 98.0%

methanol (67-56-1) + endo-1-bromo-4,4-dimethyl-3,5,8-trioxatricyclo[5.2.2.0]undec-10-en-9-one (134593-84-3,134678-33-4) → (1R,4R,5S,6S)-1-Bromo-4,5,6-trihydroxy-cyclohex-2-enecarboxylic acid methyl ester (134593-85-4)

Guidance literature:

With toluene-4-sulfonic acid; for 17h;

DOI:10.1021/jo00014a003

Reference yield:

3-bromo-2H-pyran-2-one (19978-32-6) → (1R,4R,5S,6S)-1-Bromo-4,5,6-trihydroxy-cyclohex-2-enecarboxylic acid methyl ester (134593-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / i-Pr₂NEt / CH₂Cl₂ / 4 h / 90 °C

2: 98 percent / p-TsOH / 17 h

With toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo00014a003

Reference yield: 100.0%

t-butyldimethylsiyl triflate (69739-34-0) + (1R,4R,5S,6S)-1-Bromo-4,5,6-trihydroxy-cyclohex-2-enecarboxylic acid methyl ester (134593-85-4) → (1S,4S,5R,6R)-1-Bromo-4,5,6-tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enecarboxylic acid methyl ester (134593-86-5)

Guidance literature:

With 2,6-dimethylpyridine; dmap; In dichloromethane;

DOI:10.1021/jo00014a003

upstream raw materials:

methanol

endo-1-bromo-4,4-dimethyl-3,5,8-trioxatricyclo[5.2.2.0]undec-10-en-9-one

3-bromo-2H-pyran-2-one

Downstream raw materials:

(1S,4S,5R,6R)-1-Bromo-4,5,6-tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enecarboxylic acid methyl ester

[(4S,5R,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-methanol

2-[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethanol

(1S,2R,3S)-1,2,3-Tris-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-eth-(Z)-ylidene]-4-methylene-cyclohexane

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