Phenyl alpha-D-glucopyranoside

Base Information

• Chemical Name: Phenyl alpha-D-glucopyranoside
• CAS No.: 4630-62-0
• Molecular Formula: C12H16 O6
• Molecular Weight: 256.255
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID401311850
• Nikkaji Number: J304.571D
• Wikidata: Q105178305
• ChEMBL ID: CHEMBL4104653
• Mol file: 4630-62-0.mol

Synonyms:Phenyl alpha-D-glucopyranoside;4630-62-0;Phenyl alpha-D-glucoside;phenyl |A-d-glucopyranoside;PHENYLALPHA-D-GLUCOPYRANOSIDE;alpha-D-Glucopyranoside, phenyl-;Glucopyranoside, phenyl, alpha-D-;phenyl-alpha-D-glucoside;alpha-D-Glucopyranose phenyl glycoside;NSC 226967;a-D-Glucopyranoside, phenyl;BRN 0087520;Phenyl a-D-glucopyranoside;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol;4-17-00-02944 (Beilstein Handbook Reference);C12H16O6;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-phenoxy-oxane-3,4,5-triol;PHENYL-alpha-D-GLUCOPYRANOSIDE;phenyl -d-glucoside;SCHEMBL187908;Phenyl alpha -D-glucopyranoside;CHEMBL4104653;DTXSID401311850;MFCD00006594;HY-W145603;O(c1ccccc1)C2OC(CO)C(O)C(O)C2O;LS-71579;CS-0226029;P1346;D92119;(2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-phenoxytetrahydro-2H-pyran-3,4,5-triol;7OL

Chemical Property of Phenyl alpha-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 4.17E-10mmHg at 25°C
• Melting Point: 172 °C
• Refractive Index: 180 ° (C=1, H2O)
• Boiling Point: 482.1 °C at 760 mmHg
• Flash Point: 245.4 °C
• PSA: 99.38000
• Density: 1.451 g/cm³
• LogP: -1.13470
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• 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 a-D-Glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

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: Inhibits sucrose transport into plant cells

Technology Process of Phenyl alpha-D-glucopyranoside

There total 19 articles about Phenyl alpha-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: 96.0%

phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (3427-45-0) → phenyl-α-D-glucopyranoside (4630-62-0)

Guidance literature:

With sodium methylate; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(98)00935-1

Reference yield: 90.0%

phenyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside (77874-29-4) → phenyl-α-D-glucopyranoside (4630-62-0)

Guidance literature:

With sodium methylate; In methanol; for 18h;

DOI:10.1039/b316728c

Reference yield: 65.0%

phenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside (1259428-56-2) → phenyl α-D-mannoopyranoside (1464-44-4,2818-58-8,2871-15-0,3332-35-2,3443-20-7,4630-62-0,15548-42-2,21797-50-2,28278-26-4,34246-15-6,39031-68-0,39031-69-1,56390-15-9,99530-31-1,104759-98-0)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; Inert atmosphere;

DOI:10.1021/jm101011y

upstream raw materials:

phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

D-Mannose pentaacetate

phenol

β-D-mannopyranose pentaacetate

Downstream raw materials:

phenyl-6-O-trityl-α-D-glucopyranoside

Phenyl-O-(α-D-glucopyranosyl)-(1->4)-(α-D-glucopyranosyl)-(1->4)-D-glucopyranosid

phenyl α-maltoside

phenyl (S)-2,3:4,6-O-di-benzylidene-α-D-mannopyranoside

Refernces

• 1、 Sato, Toshiyuki,Hasegawa, Nobukazu,Saito, Jun,Umezawa, Satoru,Honda, Yuki,Kino, Kuniki,Kirimura, Kohtaro. "Purification, characterization, and gene identification of an α-glucosyl transfer enzyme, a novel type α-glucosidase from Xanthomonas campestris WU-9701". body text. p. 20 - 27. Retrieved 2012/09/05.
• 2、 Klein, Tobias,Abgottspon, Daniela,Wittwer, Matthias,Rabbani, Said,Herold, Janno,Jiang, Xiaohua,Kleeb, Simon,Lüthi, Christine,Scharenberg, Meike,Bezen?on, Jacqueline,Gubler, Erich,Pang, Lijuan,Smiesko, Martin,Cutting, Brian,Schwardt, Oliver,Ernst, Beat. "FimH antagonists for the oral treatment of urinary tract infections: From design and synthesis to in vitro and in vivo evaluation". supporting information; experimental part. p. 8627 - 8641. Retrieved 2011/02/28.