151909-91-0

Basic information

• Product Name: isopropyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside
• Synonyms: isopropyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside
• CAS NO: 151909-91-0
• Molecular Weight: 582.737
• Mol File: 151909-91-0.mol

Chemical Properties

• CAS DataBase Reference: isopropyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: isopropyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside(151909-91-0)
• EPA Substance Registry System: isopropyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside(151909-91-0)

Safety Data

• Hazardous Substances Data: 151909-91-0(Hazardous Substances Data)

Upstream product

• 67-63-0 isopropyl alcohol 
• 1462249-30-4 C₄₆H₄₃N₂O₁₃P 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 79386-43-9 diphenyl 2,3,4,6-tetra-O-benzyl-α-D-glucosyl phosphate 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 67773-43-7 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide 
• 139293-33-7 2-((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrimidine 
• 139293-32-6 (E)-3-Phenyl-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid ethyl ester 
• 1927-70-4 2-isopropoxytetrahydropyran 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 132201-75-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 

Relevant articles and documents

NMR evidence for the participation of triflated ionic liquids in glycosylation reaction mechanisms

A systematic low-temperature NMR study of a glycosylation reaction was performed in the presence of different ionic liquids and acidic catalysts. The influence of the triflate anion derived from [emim][OTf] on the stereochemistry of the glycosylation prod

Glycosyl sulfates as glycosyl donors

Glycosyl sulfates are easily synthesised from tetrabenzyl pyranoses; their reaction with various acceptors promoted by Lewis acids affords glycosides and disaccharides as α,β mixtures.

Gold(III)-Catalyzed Glycosylation using Phenylpropiolate Glycosides: Phenylpropiolic Acid, An Easily Separable and Reusable Leaving Group

An efficient and operationally simple gold(III)-catalyzed glycosylation protocol was developed using newly synthesized benchtop stable phenylpropiolate glycosyl (PPG) donors. Gold(III)-catalyzed activation of PPGs proceeds well with various carbohydrate a

REAGENTS AND METHODS FOR GLYCOSYLATION

The invention provides methods and regents for the glycosylation of organic molecules. In one aspect, the invention provides a method for glycosylating a hydroxyl-containing organic compound (i.e., a glycosyl acceptor) comprising contacting a glycosyl don

Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors

The glycosylation of O-glycosyl trichloroacetimidate donors using a synergistic catalytic system of electron-deficient pyridinium salts/aryl thiourea derivatives at room temperature is demonstrated. The acidity of the adduct formed by the 1, 2-addition of

Photo-induced glycosylation using reusable organophotoacids

The glycosylation reactions of glycosyl trichloroacetimidates and several alcohols using an organophotoacid as an activator under photoirradiation proceeded smoothly to give the corresponding glycosides in high yields. The organophotoacid was recovered and reused without any loss of efficiency. This journal is the Partner Organisations 2014.

Cooperative catalysis in glycosidation reactions with o-glycosyl trichloroacetimidates as glycosyl donors

Thiourea mediates cooperative glycosidation through hydrogen bonding. N,N′-Diarylthiourea as cocatalyst enforces an SN2-type acid-catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From O-(α-glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, β-glycosides are preferentially or exclusively obtained.

Glycoside bond formation via acid-base catalysis

Acid-base catalyzed glycosyl donor and then glycosyl acceptor activation with phenylboron difluoride or diphenylboron fluoride permits hydrogen bond mediated intramolecular SN2-type glycosidation in generally high anomeric selectivity.

Glycosyl trichloroacetylcarbamate: A new glycosyl donor for O-glycosylation

Glycosyl trichloroacetylcarbamates, readily obtained by reacting 1-hydroxy sugars with trichloroacetylisocyanate, have been found as excellent glycosyl donors, and the corresponding O-glycosides are formed in good to excellent yields with a fairly good degree of selectivity.

Glycosylation with trichloroacetimidates in ionic liquids: Influence of the reaction medium on the stereochemical outcome

The glycosylation with trichloroacetimidates derived from different glycopyranoses bearing a nonparticipating group at C-2 was explored in different ionic liquids as solvents. The stereoselectivity of the reaction was significantly affected by the reactio