123632-51-9

Basic information

• Product Name: (2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl benzoate
• Synonyms: (2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl benzoate
• CAS NO: 123632-51-9
• Molecular Weight: 284.266
• Mol File: 123632-51-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl benzoate(123632-51-9)
• EPA Substance Registry System: (2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl benzoate(123632-51-9)

Safety Data

• Hazardous Substances Data: 123632-51-9(Hazardous Substances Data)

Upstream product

• 492-62-6 alpha-D-glucopyranose 
• 65-85-0 benzoic acid 
• 81336-89-2 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triol 
• 81342-44-1 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 117252-71-8 2-(trimethylsilyl)ethyl 2,3,4,6-tetrakis-O-(trifluoroacetyl)-β-D-glucopyranoside 
• 170428-69-0 C₁₂H₁₇NO₇ 
• 170428-43-0 C₂₀H₂₅NO₁₁ 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Relevant articles and documents

Solvent-Dependent Mechanism and Stereochemistry of Mitsunobu Glycosylation with Unprotected Pyranoses

An SN2 mechanism was proposed for highly stereoselective glycosylation of benzoic acid with unprotected α-d-glucose under Mitsunobu conditions in dioxane, while an SN1 mechanism was indicated for nonstereoselective glycosylation in DMF. The SN2-type stereoselective Mitsunobu glycosylation is generally applicable to various unprotected pyranoses as glycosyl donors in combination with a wide range of acidic glycosyl acceptors such as carboxylic acids, phenols, and imides, retaining its high stereoselectivity (33 examples). Glycosylation of a carboxylic acid with unprotected α-d-mannose proceeded also in an SN2 manner to directly afford a usually less accessible 1,2-cis-mannoside. One-or two-step total syntheses of five simple natural glycosides were performed using the glycosylation strategy presented here using unprotected α-d-glucose.

Hydroxy protection groups

The present invention concerns a method for preparing unprotected hydroxy compounds or acylated derivatives thereof by conversion of silyl alkyl-protected hydroxy compounds. The invention also relates to novel intermediates useful in the method and for other purposes.