Phenyl beta-D-glucopyranoside

Base Information

• Chemical Name: Phenyl beta-D-glucopyranoside
• CAS No.: 1464-44-4
• Deprecated CAS: 30370-91-3,62505-72-0,1078791-74-8
• Molecular Formula: C12H16 O6
• Molecular Weight: 256.255
• Hs Code.: 29400090
• European Community (EC) Number: 215-978-6
• UNII: 4W3PGI3766
• DSSTox Substance ID: DTXSID40883677
• Nikkaji Number: J149.732D
• Wikidata: Q27107738
• Metabolomics Workbench ID: 67804
• ChEMBL ID: CHEMBL4105357
• Mol file: 1464-44-4.mol

Synonyms:phenyl beta-D-glucopyranoside;phenyl-beta-glucoside;phenylglucoside;phenylglucoside, (alpha-(D))-isomer;phenylglucoside, (alpha-(L))-isomer

Chemical Property of Phenyl beta-D-glucopyranoside

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 176-178 °C(lit.)
• Refractive Index: -70.5 ° (C=2, H2O)
• Boiling Point: 482.1 °C at 760 mmHg
• PKA: 12.70±0.70(Predicted)
• Flash Point: 245.4 °C
• PSA: 99.38000
• Density: 1.451 g/cm³
• LogP: -1.13470
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly, Sonicated)
• Water Solubility.: Soluble in water
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 256.09468823
• Heavy Atom Count: 18
• Complexity: 255

Purity/Quality:

98%, ^*data from raw suppliers

Phenyl b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Safety Statements: 16-26-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• 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.

Technology Process of Phenyl beta-D-glucopyranoside

There total 33 articles about Phenyl beta-D-glucopyranoside 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: 99.0%

(-)-(4,6-O-benzylidene)phenyl-β-D-glucopyranoside (54502-82-8) → phenyl-β-D-glucopyranoside (1464-44-4)

Guidance literature:

With water; at 120 ℃; for 0.5h; microwave irradiation;

DOI:10.1016/j.tetlet.2007.10.038

Reference yield: 97.0%

phenyl 4,6-O-(2,5-dihydroxybenzylidene)-β-D-glucopyranoside (1079921-54-2) → 2,5-Dihydroxybenzaldehyde (1194-98-5) + phenyl-β-D-glucopyranoside (1464-44-4)

Guidance literature:

With water; In methanol; Quantum yield; Irradiation;

DOI:10.1021/ol802141g

Reference yield: 96.0%

phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4468-72-8) → phenyl-β-D-glucopyranoside (1464-44-4)

Guidance literature:

With sodium methylate; In methanol; for 0.5h;

DOI:10.1021/ja903322w

upstream raw materials:

1-deoxy-1-fluoro-α-D-glucose

phenol

Phenyl-2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosid

ethanol

Downstream raw materials:

phenyl 4,6-O-para-methoxybenzylidene-β-D-glucopyranoside

β-D-glucose

(-)-(4,6-O-benzylidene)phenyl-β-D-glucopyranoside

phenyl β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside

Refernces

• 1、 Fairbanks, Antony J.,Qiu, Xin. "Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution". . p. 7355 - 7365. Retrieved 2020/10/13.
• 2、 Nasibullin,Valiev,Faiskanova,Stepanova,Cherepanov,Filimonov,Sundholm. "Deacetylation of per-acetatylated glycopyranosides: An overall pattern for acidic catalyzis". . p. 123 - 127. Retrieved 2019/03/26.