PHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE

Base Information

• Chemical Name: PHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE
• CAS No.: 2872-72-2
• Molecular Formula: C20H24 O10
• Molecular Weight: 424.405
• European Community (EC) Number: 220-705-9
• DSSTox Substance ID: DTXSID201225803
• Nikkaji Number: J306.789K
• Mol file: 2872-72-2.mol

Synonyms:Galactopyranoside,phenyl, tetraacetate (6CI,7CI); Galactopyranoside, phenyl, tetraacetate, b-D- (8CI); NSC 173175; Phenyl2,3,4,6-tetra-O-acetyl-b-D-galactopyranoside; Phenyl tetra-O-acetyl-b-D-galactopyranoside

Chemical Property of PHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE

Chemical Property:

• Melting Point: 123-124 °C
• Boiling Point: 491.4°Cat760mmHg
• Flash Point: 212°C
• PSA: 123.66000
• Density: 1.29g/cm³
• LogP: 1.14850
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 424.13694696
• Heavy Atom Count: 30
• Complexity: 627

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC2=CC=CC=C2)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=CC=C2)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: Phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (cas# 2872-72-2) is a compound useful in organic synthesis.

Technology Process of PHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE

There total 24 articles about PHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE 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: 95.0%

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) + phenol (108-95-2,27073-41-2) → phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-72-2)

Guidance literature:

With potassium carbonate; for 0.75h; Neat (no solvent);

DOI:10.1080/07328300802402259

Reference yield: 78.0%

diphenyldisulfane (882-33-7) + β-D-galactose peracetate (4163-60-4) → phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-72-2) + (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-phenoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (18463-30-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; at 20 ℃; for 1h; Ionic liquid;

DOI:10.1055/s-0030-1260966

Reference yield: 77.0%

phenol (108-95-2,27073-41-2) + β-D-galactose peracetate (4163-60-4) → phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-72-2)

Guidance literature:

With toluene-4-sulfonic acid; at 95 ℃; for 1.5h; under 15 Torr;

DOI:10.1016/0957-4166(95)00171-K

upstream raw materials:

phenol

β-D-galactose peracetate

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

D-galactose pentaacetate

Downstream raw materials:

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-phenoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

phenyl-[O²,O³-dibenzyl-O⁴,O⁶-((S)-benzylidene)-β-D-galactopyranoside]

phenyl-[O⁴,O⁶-((S)-benzylidene)-O²,O³-dimethyl-β-D-galactopyranoside]

phenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside

Refernces

• 1、 Dimakos, Victoria,Liu, Jacklyn J. W.,Ge, Zhenlu,Taylor, Mark S.. "Copper-mediated anomeric: O -arylation with organoboron reagents". supporting information. p. 5671 - 5674. Retrieved 2019/06/18.
• 2、 Wa?ejko, Piotr,Bukowicki, Jaros?aw,Dobrzycki, ?ukasz,Socha, Pawe?,Paradowska, Katarzyna. "Phenyl glycosides – Solid-state NMR, X-ray diffraction and conformational analysis using genetic algorithm". . p. 126 - 136. Retrieved 2019/01/03.