78617-45-5

Basic information

• Product Name: 2-(bromomethyl)phenyl tetra-O-acetyl-α-D-glucopyranoside
• Synonyms: 2-(bromomethyl)phenyl tetra-O-acetyl-α-D-glucopyranoside
• CAS NO: 78617-45-5
• Molecular Weight: 517.327
• Mol File: 78617-45-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-(bromomethyl)phenyl tetra-O-acetyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(bromomethyl)phenyl tetra-O-acetyl-α-D-glucopyranoside(78617-45-5)
• EPA Substance Registry System: 2-(bromomethyl)phenyl tetra-O-acetyl-α-D-glucopyranoside(78617-45-5)

Safety Data

• Hazardous Substances Data: 78617-45-5(Hazardous Substances Data)

Upstream product

• 83-87-4 D-glucose pentaacetate 
• 106-44-5 p-cresol 
• 32742-30-6 4-methylphenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 92052-29-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 
• 604-69-3 β-D-glucose pentaacetate 
• 14581-78-3 4-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 2887-07-2 4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 64291-41-4 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate 

Downstream Products

• 64291-41-4 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 53829-50-8 (4-aminomethyl-phenyl)-β-D-glucopyranoside 
• 62499-27-8 gastrodin 
• 908577-08-2 [4-(β-D-glucopyranosyloxy)phenyl]acetonitrile 
• 123403-21-4 4-(β-D-glucopyranosyloxy)benzylacetic acid 
• 161767-47-1 4-(chloromethyl)phenyl tetra-O-acetyl-α-D-glucopyranoside 

Relevant articles and documents

Improved synthesis of gastrodin, a bioactive component of a traditional chinese medicine

Highly practical, four-step synthesis of gastrodin was developed using penta- O-acetyl-β-D-glucopyranose and p-cresol as glycosyl donor and glycosyl acceptor, respectively, in 58.1% overall yield. As the initial step, the penta-O-acetyl-β-D-glucopyranose was treated with p-cresol in the presence of BF3 ?Et2O as catalyst to generate 4-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D- -glucopyranoside in 76.3% yield. Further, this product was subjected to radical bromination with N-bromosuccinimide (NBS) to provide 4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in 91% yield. Subsequently, reaction of 4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside with a solution of acetone and saturated aqueous sodium bicarbonate led to 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in 93% yield. Finally, global deprotection of 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O- -acetyl-β- D-glucopyranoside under Zemplen conditions furnished gastrodin in 90% yield. Compared to the previously reported methods, this protocol has the advantages of operational simplicity, chromatography-free separation, high overall yield, inexpensive and common reagents as well as less waste pollutants, rendering it an alternative suitable for industrial production.

DUAL PROTECTED PRO-COELENTERAZINE SUBSTRATES

Described are coelenterazine analogues, methods for making the analogues, kits comprising the analogues, and methods of using the compounds for the detection of luminescence in luciferase-based assays.

(Halogenomethyl)phenyl &α-D-Glucopyranosides as Enzyme-activated Irreversible Inhibitors of Yeast &α-Glucosidase and Potential Anti-HIV Agents

A range of (halogenomethyl)phenyl α-D-glucopyranosides 2-7, prepared from corresponding methylphenyl glucosides by synthetic manipulation of the aglycone moiety, have been investigated as enzyme-activated irreversible inhibitors of yeast α-glucosidase and