(1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-3-oxo-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-3-oxo-cyclohexanecarboxylic acid methyl ester
• CAS No.: 202416-32-8
• Molecular Formula: C₁₄H₂₅BrO₆Si
• Molecular Weight: 397.338

Synonyms:(1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-3-oxo-cyclohexanecarboxylic acid methyl ester

Chemical Property of (1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-3-oxo-cyclohexanecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-3-oxo-cyclohexanecarboxylic acid methyl ester

There total 1 articles about (1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-3-oxo-cyclohexanecarboxylic 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: 6.0%

methanol (67-56-1) + (1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-6-oxa-bicyclo[3.2.1]octane-3,7-dione (189366-38-9) → (1R,3R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-oxo-7-oxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester + (1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-3-oxo-cyclohexanecarboxylic acid methyl ester (202416-32-8)

Guidance literature:

With sodium methylate; for 0.25h;

DOI:10.1021/jo971858i

Reference yield: 90.0%

trifluoroacetic anhydride (407-25-0) + (1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-3-oxo-cyclohexanecarboxylic acid methyl ester (202416-32-8) → (4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-5-(2,2,2-trifluoro-acetoxy)-cyclohex-1-enecarboxylic acid methyl ester (202416-35-1)

Guidance literature:

In pyridine; dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jo971858i

Reference yield: 84.0%

(1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-3-oxo-cyclohexanecarboxylic acid methyl ester (202416-32-8) → (1R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,5-dihydroxy-4-oxo-cyclohex-2-enecarboxylic acid methyl ester

Guidance literature:

With triethylamine; In dichloromethane; for 8h; Ambient temperature;

DOI:10.1021/jo971858i

upstream raw materials:

methanol

(1S,2R,4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-6-oxa-bicyclo[3.2.1]octane-3,7-dione

Downstream raw materials:

(4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-5-(2,2,2-trifluoro-acetoxy)-cyclohex-1-enecarboxylic acid methyl ester

(4S,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-cyclohex-1-enecarboxylic acid methyl ester

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