21056-52-0

Basic information

• Product Name: Benzoyl β-D-glucopyranoside
• Synonyms: Benzoyl β-D-glucopyranoside;Periplanetin
• CAS NO: 21056-52-0
• Molecular Formula: C₁₃H₁₆O₇
• Molecular Weight: 284.26194
• Mol File: 21056-52-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 193 °C
• Boiling Point: 507.1°C at 760 mmHg
• Flash Point: 194.1°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 4.19E-11mmHg at 25°C
• Refractive Index: 1.625
• PKA: 12?+-.0.70(Predicted)
• CAS DataBase Reference: Benzoyl β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoyl β-D-glucopyranoside(21056-52-0)
• EPA Substance Registry System: Benzoyl β-D-glucopyranoside(21056-52-0)

Safety Data

• Hazardous Substances Data: 21056-52-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H16O7/c14-6-8-9(15)10(16)11(17)13(19-8)20-12(18)7-4-2-1-3-5-7/h1-5,8-11,13-17H,6H2

Upstream product

• 63053-84-9 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose 
• 65-85-0 benzoic acid 
• 492-62-6 alpha-D-glucopyranose 
• 170428-69-0 C₁₂H₁₇NO₇ 
• 170428-43-0 C₂₀H₂₅NO₁₁ 
• 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 
• 98-88-4 benzoyl chloride 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 117252-71-8 2-(trimethylsilyl)ethyl 2,3,4,6-tetrakis-O-(trifluoroacetyl)-β-D-glucopyranoside 

Downstream Products

• 38430-69-2 O²,O³,O⁴,O⁶-Tetraacetyl-O¹-benzoyl-β-D-glucopyranose 

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.

Simple Synthesis of β-D-Glucosyl Esters

Acylation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (1) with benzoyl chloride and triethylamine was found to give 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (2) and 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose (3) in a ratio of 2:9 whi

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.