141564-18-3

Basic information

• Product Name: 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• Synonyms: 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• CAS NO: 141564-18-3
• Molecular Weight: 622.681
• Mol File: 141564-18-3.mol

Chemical Properties

• CAS DataBase Reference: 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside(141564-18-3)
• EPA Substance Registry System: 2,2,2-trifluoroethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside(141564-18-3)

Safety Data

• Hazardous Substances Data: 141564-18-3(Hazardous Substances Data)

Upstream product

• 194088-19-2 (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran 
• 75-89-8 2,2,2-trifluoroethanol 
• 604-69-3 β-D-glucose pentaacetate 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 56822-48-1 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl acetate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Relevant articles and documents

How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?

The reaction of glycosyl donor phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with NIS/TfOH(cat.) was systematically studied under various reaction conditions. Neither the molecular sieve pore size nor amount of NIS activator was found to have a

An Unexpected FeCl 3/C-Catalyzed β-Stereoselective Glycosylation in the Presence of the C(2)-Benzyl Group

An efficient and completely β-stereoselective glycosylation that did not rely on neighboring group participation is described using 2-20 molpercent FeCl 3 /C as the catalyst and benzylated propargyl glycosides as the donors to reach yields up to 96percent under mild condition. With an octatomic-ring intermediate at the α-face of FeCl 3 /C with alkyne of propargyl glycosides, a panel of aglycones comprising aliphatic, alicyclic, unsaturated alcohols, halogenated alcohols, and phenols with different substitution were examined successfully for the exclusive β-stereoselective glycosylation reaction.

Variations on the SnCl4 and CF3CO2Ag-promoted glycosidation of sugar acetates: a direct, versatile and apparently simple method with either α or β stereocontrol

Glycosidation of sugar peracetates (d-gluco, d-galacto) with SnCl4 and CF3CO2Ag led to either 1,2-cis-, or 1,2-trans-glycosides, depending primarily on the alcohols used. In particular, 1,2-trans-glycosides, expected from acyl-protected glycosyl donors, were formed in high yields with alcohols sharing specific features such as bulkiness, presence of electron-withdrawing groups or polyethoxy motifs. In contrast, simple alcohols afforded ～1:1 mixtures of 2,3,4,6-tetra-O-acetyl, and 3,4,6-tri-O-acetyl 1,2-cis-glycosides due to anomerization and/or acid-catalyzed fragmentation of 1,2-orthoester intermediates. After reacetylation or deacetylation, acetylated or fully deprotected 1,2-cis-glycosides (α-d-gluco, α-d-galacto) were obtained in ～90% yields by a simple and direct method.

A convenient synthesis of fluoroalkyl and fluoroaryl glycosides using Mitsunobu conditions

A new procedure for the synthesis of fluoroalkyl and fluoroaryl glycosides from primary, secondary, and tertiary fluoroalkyl alcohols and pentafluorophenol using Mitsunobu conditions is reported. Copyright (C) 1999 Elsevier Science Ltd.

Dehydroxy substitution reactions of the anomeric hydroxy groups in some protected sugars initiated by anodic oxidation of triphenylphosphine

The anodic transformation of 2,3:5,6-di-O-isopropylidene-α-D- mannofuranose (4) and 2,3,4,6-tetra-O-benzyl-D-glucopyranose (5) to the corresponding alkoxy phosphonium ions induces dehydroxy substitution of the sugars at the anomeric positions. Their dehyd