73111-14-5

Basic information

• Product Name: 3,4,5-tris(benzyloxy)-2-(bromomethyl)-6-methoxytetrahydro-2H-pyran
• Synonyms: 3,4,5-tris(benzyloxy)-2-(bromomethyl)-6-methoxytetrahydro-2H-pyran
• CAS NO: 73111-14-5
• Molecular Weight: 527.455
• Mol File: 73111-14-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3,4,5-tris(benzyloxy)-2-(bromomethyl)-6-methoxytetrahydro-2H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-tris(benzyloxy)-2-(bromomethyl)-6-methoxytetrahydro-2H-pyran(73111-14-5)
• EPA Substance Registry System: 3,4,5-tris(benzyloxy)-2-(bromomethyl)-6-methoxytetrahydro-2H-pyran(73111-14-5)

Safety Data

• Hazardous Substances Data: 73111-14-5(Hazardous Substances Data)

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 7465-44-3 methyl 6-bromo-6-deoxy-α-D-glucopyranoside 
• 1079205-73-4 C₃₇H₅₂O₆Si 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 

Downstream Products

• 73111-18-9 (3aR)-4c,5t,6c-tris-benzyloxy-1-methyl-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole 
• 1461750-25-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one 
• 73174-45-5 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 
• 19139-89-0 (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 
• 155480-22-1 methyl 2,3,4-tri-O-benzyl-6,7,8,9-tetradeoxy-α-D-gluco-non-8-enopyranoside 
• 73111-47-4 (3aR,3'aR)-4c,5t,6c,4'c',5't',6'c'-hexakis-benzyloxy-(3ar,6ac,3'ar',6'ac')-dodecahydro-1,1'-methanediyl-bis-cyclopenta[c]isoxazole 
• 73111-42-9 (4aR)-5c,6t,7c-tris-benzyloxy-1-methyl-(4ar,7ac)-hexahydro-cyclopenta[d][1,3]oxazine 
• 134784-89-7 6-((2R,3S,4R,5R,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-hydroxymethyl-1-oxy-piperidin-2-yl)-2-chloro-hexan-1-ol 
• 134784-91-1 [(2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-(4-oxiranyl-butyl)-1-oxy-piperidin-2-yl]-methanol 
• 134820-80-7 ((2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-hex-5-enyl-piperidin-2-yl)-methanol 
• 134930-15-7 (3R,4S,5S,6R)-6-amino-(N-benzyl)-3,4,5-tribenzyloxydodeca-1,11-diene 
• 134784-88-6 (3R,4S,5S,6S)-6-amino-(N-benzyl)-3,4,5-tribenzyloxydodeca-1,11-diene 
• 134820-81-8 (2R,3S,4R,5R,6R)-1-Benzyl-2-(5-chloro-6-hydroxy-hexyl)-6-hydroxymethyl-piperidine-3,4,5-triol 
• 134784-87-5 (3R,4S,5S)-3,4,5-tribenzyloxydodeca-1,11-dien-6-one 

Relevant articles and documents

Design, synthesis and biological evaluation of 6-deoxy O-spiroketal C-arylglucosides as novel renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes

In this work, aiming at finding a novel, potent, and selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor with good pharmacokinetic profiles for the treatment of diabetes, we focus on modifying the sugar moiety of SGLT2 inhibitors, which dominates the binding with glucose binding site of hSGLT, via removing the C-6 hydroxy group to adjust the physicochemical properties and target-recognition manners of SGLT2 inhibitors. In addition, tofogliflozin containing a special O-spiroketal C-arylglucoside scaffold, displayed good efficacy and bioavailability both in animals and in humans. Therefore, a series of 6-deoxy O-spiroketal C-arylglucosides as novel SGLT2 inhibitors were designed, synthesized, and evaluated in this work. The structure-activity relationship (SAR) research on this novel series and a comprehensive in vitro and in vivo biological evaluation afforded compound 39 with high in vitro hSGLT2 inhibitory activity (IC50 = 4.5 nM), good pharmacokinetic profiles, and more remarkable efficacy in C57BL/6J mice and Sprague-Dawley rats than marketed drug tofogliflozin.

Conversion of D-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction: Application to Total Synthesis of (+)-Cyclophellitol

(Matrix presented). A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4, 5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cyclo

Solvent-free benzylation of polyols by phase-transfer catalysis or supported reagent methods

Solvent-free techniques were successfully and efficiently applied under mild conditions to the perbenzylation of methyl α-D-glucopyranoside and methyl 6-bromo(and 6-chloro)-6-deoxy-α-D-glucopyranoside, and to the selective monobenzylation of diethyl (R,R)