32741-93-8

Basic information

• Product Name: 1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate
• Synonyms: 1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate
• CAS NO: 32741-93-8
• Molecular Weight: 248.043
• Mol File: 32741-93-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate(32741-93-8)
• EPA Substance Registry System: 1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate(32741-93-8)

Safety Data

• Hazardous Substances Data: 32741-93-8(Hazardous Substances Data)

Upstream product

• 498-07-7 levoglucosan 
• 98-80-6 phenylboronic acid 

Downstream Products

• 5627-22-5 (2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triol 
• 137334-33-9 1,6-anhydro-3-O-β-D-glucopyranosyl-β-D-glucopyranose 
• 842133-18-0 canagliflozin 
• 498-07-7 levoglucosan 
• 98-80-6 phenylboronic acid 

Relevant articles and documents

β-Selective C-Arylation of Diisobutylaluminum Hydride Modified 1,6-Anhydroglucose: Synthesis of Canagliflozin without Recourse to Conventional Protecting Groups

The β-selective phenylation of benzyl and boronate protected 1,6-anhydroglucose and the direct phenylation of unprotected 1,6-anhydroglucose (10), pretreated with i-Bu2AlH, i-Bu3Al, Et3Al, Me3Al, or n-octyl3Al, with triphenylalane or aryl(chloro)alanes is reported. The utility of the unprotected version of the method is demonstrated by the synthesis of the SGLT2 inhibitor, canagliflozin (1a), from commercially available 10 in one C-C bond-forming step. This approach circumvents the need for conventional protecting groups, and therefore no formal protection and deprotection steps are required. (Chemical Presented).