Phenylethyl beta-D-glucopyranoside

Base Information

• Chemical Name: Phenylethyl beta-D-glucopyranoside
• CAS No.: 18997-54-1
• Molecular Formula: C₁₄H₂₀O₆
• Molecular Weight: 284.309
• European Community (EC) Number: 803-387-1
• ChEMBL ID: CHEMBL510617
• DSSTox Substance ID: DTXSID801303726
• Metabolomics Workbench ID: 140921
• Nikkaji Number: J254.145I
• Wikidata: Q105167009
• Mol file: 18997-54-1.mol

Synonyms:18997-54-1;Phenylethyl beta-D-glucopyranoside;(2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-phenethoxytetrahydro-2H-pyran-3,4,5-triol;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-phenylethoxy)oxane-3,4,5-triol;Phenylethyl 2-Glucoside;2-Phenylethyl b-D-glucopyranoside;Phenylethyl b-D-glucopyranoside;|A-Phenylethyl |A-D-Glucoside;CHEMBL510617;MEGxp0_000929;SCHEMBL8843011;ACon1_001188;CHEBI:182253;2-Phenylethyl-beta-glucopyranoside;DTXSID801303726;2-phenylethyl-beta-d-glucopyranoside;beta -Phenylethyl beta -D-Glucoside;AKOS027327179;2-Phenylethyl O-beta-D-Glucopyranoside;FS-8496;NCGC00169593-01;NCGC00169593-02;BRD-K59028558-001-01-0;2-Phenylethyl beta-D-glucopyranoside, >=95% (LC/MS-ELSD)

Chemical Property of Phenylethyl beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 2.73E-10mmHg at 25°C
• Refractive Index: 1.6
• Boiling Point: 486.8°C at 760 mmHg
• Flash Point: 248.2°C
• PSA: 99.38000
• Density: 1.36g/cm³
• LogP: -0.95440
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 284.12598835
• Heavy Atom Count: 20
• Complexity: 281

Purity/Quality:

98%min ^*data from raw suppliers

β-Phenylethylβ-D-Glucoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCOC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)CCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: One of the two new glycosides from Conyza bonariensis. One of the two new glycosides from Conyza bonariensis

Technology Process of Phenylethyl beta-D-glucopyranoside

There total 22 articles about Phenylethyl 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: 92.0%

2-phenylethanol 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (76870-86-5,76870-87-6,94591-54-5,94591-55-6,134698-99-0) → 2-phenylethyl-β-D-glucopyranoside (14861-16-6,18997-54-1,23508-41-0,58716-72-6,105088-18-4,134733-76-9,142696-65-9)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 2h;

DOI:10.1248/cpb.58.1627

Reference yield: 87.0%

2-phenylethyl 3,4,6-tri-O-benzyl-2-O-benzyloxycarbonyl-β-D-glucopyranoside → 2-phenylethyl-β-D-glucopyranoside (14861-16-6,18997-54-1,23508-41-0,58716-72-6,105088-18-4,134733-76-9,142696-65-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1039/c9cc07194f

Reference yield: 34.0%

D-Glucose (2280-44-6) + 2-phenylethanol (60-12-8) → 2-phenylethyl-β-D-glucopyranoside (14861-16-6,18997-54-1,23508-41-0,58716-72-6,105088-18-4,134733-76-9,142696-65-9)

Guidance literature:

With immobilized β-D-glucosidase (EC 3.2.1.21); In water; at 50 ℃; for 96h;

DOI:10.3987/COM-05-10383

upstream raw materials:

D-Glucose

2-phenylethanol

2-phenylethanol 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

phenyl-β-D-glucopyranoside

Downstream raw materials:

2'-phenylethyl β-D-glucopyranosiduronic acid

2-phenylethyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→3)-2-O-acetyl-β-D-glucopyranoside

2-phenylethyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→3)-2-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside

2-phenylethyl 4,6-O-benzylidene-β-D-glucopyranoside

Refernces

• 1、 Weber, Julia,Svatunek, Dennis,Krauter, Simon,Tegl, Gregor,Hametner, Christian,Kosma, Paul,Mikula, Hannes. "2-: O-Benzyloxycarbonyl protected glycosyl donors: A revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation". supporting information. p. 12543 - 12546. Retrieved 2019/10/28.
• 2、 De Winter, Karel,Van Renterghem, Lisa,Wuyts, Kathleen,Pelantová, Helena,K?en, Vladimír,Soetaert, Wim,Desmet, Tom. "Chemoenzymatic synthesis of β-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum". . p. 1961 - 1969. Retrieved 2015/06/02.