(2R,3S,4S,5R)-5,6-Diacetoxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid

Base Information

Chemical Name:(2R,3S,4S,5R)-5,6-Diacetoxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid
CAS No.:735326-87-1
Molecular Formula:C₁₇H₂₀O₉
Molecular Weight:368.34
Hs Code.:

Synonyms:(2R,3S,4S,5R)-5,6-Diacetoxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid

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Chemical Property of (2R,3S,4S,5R)-5,6-Diacetoxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid

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Technology Process of (2R,3S,4S,5R)-5,6-Diacetoxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid

There total 4 articles about (2R,3S,4S,5R)-5,6-Diacetoxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid 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: 61.0%

: 735326-79-1
1,2-di-O-acetyl-3-O-benzyl-L-idopyranose

: 735326-87-1
(2R,3S,4S,5R)-5,6-Diacetoxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: 1,2-di-O-acetyl-3-O-benzyl-L-idopyranose; With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite;

With potassium hydrogencarbonate; In N,N-dimethyl-formamide;

Reference yield:

: 781657-58-7
1,2-di-O-acetyl-3-O-benzyl-4,6-(R)-O-benzylidene-L-idopyranose

: 735326-87-1
(2R,3S,4S,5R)-5,6-Diacetoxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 61 percent / CF₃COOH / CH₂Cl₂; H₂O / 4 h / 0 °C

2: 1.0 g / NaOCl; TEMPO; Bu₄NBr / CH₂Cl₂; H₂O / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutylammomium bromide; trifluoroacetic acid; In dichloromethane; water;
DOI:10.1016/j.carres.2004.03.006

Reference yield:

: 3-O-benzyl-4,6-(R)-O-benzylidene-L-idopyranose

: 735326-87-1
(2R,3S,4S,5R)-5,6-Diacetoxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / pyridine / 20 h / 20 °C

2: 61 percent / CF₃COOH / CH₂Cl₂; H₂O / 4 h / 0 °C

3: 1.0 g / NaOCl; TEMPO; Bu₄NBr / CH₂Cl₂; H₂O / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutylammomium bromide; trifluoroacetic acid; In pyridine; dichloromethane; water;
DOI:10.1016/j.carres.2004.03.006