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1464-44-4

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1464-44-4 Usage

Chemical Properties

white powder

Uses

Phenyl β-D-glucopyranoside can be used:As a starting material for the synthesis of various derivatives of β-D-glucopyranosides with potential application as anti-HIV agents.As a model for glycosides in the gas phase for their spectroscopic investigation.As an internal standard in GC and GC-MS quantitative analyses.

Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating vapors.

Purification Methods

Phenyl--D-glucopyranoside recrystallises from H2O with 2H2O and can be dried in vacuo at 100o/P2O5. The dry preparation has [] 25D -70.7o (c 2, H2O). [Robertson & Waters J Chem Soc 2729 1930, IR: Bunton et al. J Chem Soc 4419 1955, Takahashi Yakugaku Zasshi (J Pharm Soc Jpn) 74 7436 1954, Whixtler & House Anal Chem 25 1463 1953, UV: Lewis J Am Chem Soc 57 898 1935.] It is a substrate for D-glucosidase [deBryne Eur J Biochem 102 257 1979]. [Beilstein 17 III/V 2946.]

Check Digit Verification of cas no

The CAS Registry Mumber 1464-44-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,6 and 4 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1464-44:
(6*1)+(5*4)+(4*6)+(3*4)+(2*4)+(1*4)=74
74 % 10 = 4
So 1464-44-4 is a valid CAS Registry Number.

1464-44-4 Well-known Company Product Price

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  • Aldrich

  • (292710)  Phenylβ-D-glucopyranoside  97%

  • 1464-44-4

  • 292710-5G

  • 1,064.70CNY

  • Detail
  • Aldrich

  • (292710)  Phenylβ-D-glucopyranoside  97%

  • 1464-44-4

  • 292710-25G

  • 3,627.00CNY

  • Detail

1464-44-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol

1.2 Other means of identification

Product number -
Other names Phenylglucoside

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1464-44-4 SDS

1464-44-4Relevant articles and documents

Isotope studies of the transfer of the carbon atoms of carbohydrate derivatives into aromatic compounds (especially xanthene) under degradation conditions

Ferrier,Severn,Furneaux,Miller

, p. 87 - 94 (1992)

Treatment of various 13C-carbohydrate-labelled phenyl β-D-glucopyranosides at 350°C in aqueous phenol in the presence of zinc chloride, with 13C NMR analysis of the xanthene formed as the major neutral product, indicated that the methylene carbon atom (C-9) of this compound was derived from C-1 (30%), C-2 (20%), and C-6 (50%) of the glucosyl units. In addition, 4.5% of the carbon from the sugar was incorporated into the aromatic rings of the xanthene. Mass spectrometry of the phenol produced on heating methyl α-D-glucopyranoside (50% U-13C) at 350°C for 1 h in aqueous zinc chloride showed the aromatic rings to be derived from the glucosyl moiety, partly without cleavage of the carbon chain and also after cleavage and recombination of the fragments.

Phenyl glycosides – Solid-state NMR, X-ray diffraction and conformational analysis using genetic algorithm

Wa?ejko, Piotr,Bukowicki, Jaros?aw,Dobrzycki, ?ukasz,Socha, Pawe?,Paradowska, Katarzyna

, p. 126 - 136 (2019/01/03)

The X-ray structures of 2,6-dimethylphenyl and phenyl 2,3,4,6-tetra-O-acetyl β-glucosides (1 and 3) and phenyl α-mannoside (6) were obtained. The independent part of the unit cell of the glycosides 1 and 6 was formed by one molecule, and for the glucoside 3, two molecules in the crystal cell were observed. In deacetylated glycosides 4 and 6 the crystal structure was established by a hydrogen bond network formed between the sugar hydroxyls and solvent molecules. The 13C CPMAS NMR spectra of aryl glycosides 1–6 were analysed. In the spectrum of 3, doubling of the C4 aryl signal was observed which confirmed the presence of two independent molecules in the solid sample. The GAAGS (Genetic Algorithm-Assisted Grid Search) method was used to determine the low-energy conformers of α-mannosides and β-glucosides. The orientation of the aryl pendant group was calculated using Molecular Mechanics (MMFF94) as well as Quantum Mechanics theory (DFT, B3LYP/6-31 + G(d,p)).

A new look at acid catalyzed deacetylation of carbohydrates: A regioselective synthesis and reactivity of 2-O-acetyl aryl glycopyranosides

Stepanova, Elena V.,Nagornaya, Marina O.,Filimonov, Victor D.,Valiev, Rashid R.,Belyanin, Maxim L.,Drozdova, Anna K.,Cherepanov, Victor N.

supporting information, p. 60 - 66 (2018/02/20)

In the present work we report that acetyl groups of per – acetylated aryl glycosides have different reactivity during the acidic deacetylation using HCl/EtOH in CHCl3, which leads to preferential deacetylation at O-3, O-4 and O-6. Thereby, the one-step preparation of 2-O-acetyl aryl glycosides with simple aglycon was accomplished for the first time. It was proved that the found reagent is to be general and unique for the preparation of series of 2-О-acetyl aryl glycosides. We have determined the influence of both carbohydrate moiety and the aglycon on the selectivity of deacetylation reaction by kinetic experiments. Using DFT/B3LYP/6-31G(d,p) and semi-empirical АМ1 methods we have found that the highest activation barrier is for 2-О-acetyl group. This completely explains the least reactivity of 2-О-acetyl group.

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