148905-25-3

Basic information

• Product Name: 2,3,4,6-tetra-O-benzyl-D-mannopyranosyl bromide
• Synonyms: 2,3,4,6-tetra-O-benzyl-D-mannopyranosyl bromide
• CAS NO: 148905-25-3
• Molecular Weight: 603.553
• Mol File: 148905-25-3.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-benzyl-D-mannopyranosyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-benzyl-D-mannopyranosyl bromide(148905-25-3)
• EPA Substance Registry System: 2,3,4,6-tetra-O-benzyl-D-mannopyranosyl bromide(148905-25-3)

Safety Data

• Hazardous Substances Data: 148905-25-3(Hazardous Substances Data)

Upstream product

• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 125411-99-6 ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 3866-62-4 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl acetate 
• 131531-70-9 4-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 142819-33-8 Ethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzylthio-α-D-mannopyranoside 
• 55094-26-3 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 31661-58-2 2-[4-(2-aminophenyl)-1,3-butadienyl]phenylamine 
• 924272-08-2 C₁₀₁H₁₀₈O₁₈ 

Relevant articles and documents

Bismuth(iii) triflate as a novel and efficient activator for glycosyl halides

Presented herein is the discovery that bismuth(iii) trifluoromethanesulfonate (Bi(OTf)3) is an effective catalyst for the activation of glycosyl bromides and glycosyl chlorides. The key objective for the development of this methodology is to em

Koenigs–Knorr Glycosylation Reaction Catalyzed by Trimethylsilyl Trifluoromethanesulfonate

The discovery that traditional silver(I)-oxide-promoted glycosidations of glycosyl bromides (Koenigs–Knorr reaction) can be greatly accelerated in the presence of catalytic trimethylsilyl trifluoromethanesulfonate (TMSOTf) is reported. The reaction conditions are very mild that allowed for maintaining a practically neutral pH and, at the same time, providing high rates and excellent glycosylation yields. In addition, unusual reactivity trends among a series of differentially protected glycosyl bromides were documented. In particular, benzoylated α-bromides were much more reactive than their benzylated counterparts under these conditions.

Pyranoside-into-Furanoside Rearrangement of 4-Pentenyl Glycosides in the Synthesis of a Tetrasaccharide-Related to Galactan I of Klebsiella pneumoniae

An efficient strategy for synthesis of a spacer-armed tetrasaccharide related to galactan I of Klebsiella pneumoniae is described, which uses newly developed acid-free conditions for the pyranoside-into-furanoside (PIF) rearrangement of a digalactoside bearing a 4-pentenyl group at the anomeric position. The 4-pentenyl aglycon was successfully used both as a leaving group in the glycosylation of 3-(trifluoroacetamido)propanol, and as a temporary anomeric protecting group, allowing conversion into an imidate donor. Regioselective coupling of the disaccharide blocks gave the desired tetrasaccharide sequence required for investigation of the interaction of galactan I with immune-system proteins.