(1S,3R,4R,5R)-3-(Bis-benzyloxy-phosphoryloxymethyl)-1,4,5-trihydroxy-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,3R,4R,5R)-3-(Bis-benzyloxy-phosphoryloxymethyl)-1,4,5-trihydroxy-cyclohexanecarboxylic acid methyl ester
• CAS No.: 123716-90-5
• Molecular Formula: C₂₃H₂₉O₉P
• Molecular Weight: 480.452

Synonyms:(1S,3R,4R,5R)-3-(Bis-benzyloxy-phosphoryloxymethyl)-1,4,5-trihydroxy-cyclohexanecarboxylic acid methyl ester

Chemical Property of (1S,3R,4R,5R)-3-(Bis-benzyloxy-phosphoryloxymethyl)-1,4,5-trihydroxy-cyclohexanecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (1S,3R,4R,5R)-3-(Bis-benzyloxy-phosphoryloxymethyl)-1,4,5-trihydroxy-cyclohexanecarboxylic acid methyl ester

There total 2 articles about (1S,3R,4R,5R)-3-(Bis-benzyloxy-phosphoryloxymethyl)-1,4,5-trihydroxy-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: 65.0%

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) + (1S,3R,4R,5R)-1,3,4-Trihydroxy-5-hydroxymethyl-cyclohexanecarboxylic acid methyl ester (123488-84-6) → (1S,3R,4R,5R)-3-(Bis-benzyloxy-phosphoryloxymethyl)-1,4,5-trihydroxy-cyclohexanecarboxylic acid methyl ester (123716-90-5)

Guidance literature:

With 1H-tetrazole; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)99490-5

Reference yield:

(1S,3R,4R,5R)-1,3,4-Triacetoxy-5-acetoxymethyl-cyclohexanecarboxylic acid methyl ester (123716-89-2) → (1S,3R,4R,5R)-3-(Bis-benzyloxy-phosphoryloxymethyl)-1,4,5-trihydroxy-cyclohexanecarboxylic acid methyl ester (123716-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1: KOH / methanol

2: 65 percent / tetrazole, MCPBA / CH₂Cl₂

With 1H-tetrazole; potassium hydroxide; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)99490-5

Reference yield: 97.0%

(1S,3R,4R,5R)-3-(Bis-benzyloxy-phosphoryloxymethyl)-1,4,5-trihydroxy-cyclohexanecarboxylic acid methyl ester (123716-90-5) → (1S,3R,4R,5R)-1,3,4-Trihydroxy-5-phosphonooxymethyl-cyclohexanecarboxylic acid methyl ester (123716-91-6)

Guidance literature:

With hydrogen; hydrogenolysis;

DOI:10.1016/S0040-4039(00)99490-5

upstream raw materials:

Dibenzyl N,N-diisopropylphosphoramidite

(1S,3R,4R,5R)-1,3,4-Trihydroxy-5-hydroxymethyl-cyclohexanecarboxylic acid methyl ester

(1S,3R,4R,5R)-1,3,4-Triacetoxy-5-acetoxymethyl-cyclohexanecarboxylic acid methyl ester

Downstream raw materials:

(1S,3R,4R,5R)-1,3,4-Trihydroxy-5-phosphonooxymethyl-cyclohexanecarboxylic acid methyl ester

(1S,3R,4R)-1,3,4-Trihydroxy-5-methylene-cyclohexanecarboxylic acid

(1S,3R,4R,5R)-1,3,4-Trihydroxy-5-phosphonooxymethyl-cyclohexanecarboxylic acid

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