103618-17-3

Basic information

• Product Name: (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran
• CAS NO: 103618-17-3
• Molecular Weight: 603.553
• Mol File: 103618-17-3.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran(103618-17-3)
• EPA Substance Registry System: (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran(103618-17-3)

Safety Data

• Hazardous Substances Data: 103618-17-3(Hazardous Substances Data)

Upstream product

• 125411-99-6 ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 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 
• 3866-62-4 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl acetate 

Downstream Products

• 31661-58-2 2-[4-(2-aminophenyl)-1,3-butadienyl]phenylamine 
• 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 
• 924272-08-2 C₁₀₁H₁₀₈O₁₈ 
• 252845-51-5 N-acetyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 

Relevant articles and documents

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.

Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions

A general method has been developed for the formation of glycosyl chlorides and bromides from picolinic esters under mild and neutral conditions. Benchtop stable picolinic esters are activated by a copper(II) halide species to afford the corresponding products in high yields with a traceless leaving group. Rare β glycosyl chlorides are accessible via this route through neighboring group participation. Additionally, glycosyl chlorides with labile protecting groups previously not easily accessible can be prepared.

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.

Regenerative Glycosylation

Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.

GLYCOMIMETIC INHIBITORS OF PA-IL AND PA-IIL LECTINS

Compounds, compositions, and methods for the diagnosis and/or treaimeni of medical conditions involving infections with and colonization by Fseudomonas bacteria including, for example, Fseudomonas aeruginosa in the lungs of patients with cystic fibrosis are described.

Regenerative glycosylation under nucleophilic catalysis

This article describes 3,3-difluoroxindole (HOFox)-mediated glycosylation. The uniqueness of this approach is that both the in situ synthesis of 3,3-difluoro-3H-indol-2-yl (OFox) glycosyl donors and activation thereof can be conducted in a regenerative fashion as is a typical reaction performed under nucleophilic catalysis. Only a catalytic amount of the OFox imidate donor and a Lewis acid activator are present in the reaction medium. The OFox imidate donor is constantly regenerated upon its consumption until glycosyl acceptor has reacted.

Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates

Glycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide. Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion.

New method for regioselective glycosylation employing saccharide oxyanions

As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl-α-D-glucopyranosides were used as a model system to study the underlying mechanistic principles of base-promoted glycosylation. High regioselectivities and stereospecific glycosidic bond formations were achieved, and the scope of the methodology was extended with different perbenzylated glycosyl donors.

Glycomimetic inhibitors of the PA-IL lectin, PA-IIL lectin or both the lectins from pseudomonas

Compositions and methods are provided related to Pseudomonas bacteria. The compositions and methods may be used for diagnosis and therapy of medical conditions involving infection with Pseudomonas bacteria. Such infections include Pseudomonas aeruginosa i

Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups

The efficient and elegant synthesis of N-glycosides by N-glycosylation of asparagine-containing peptides is described. Glycosylation of primary amides with glycosyl N-phenyltrifluoroimidates in the presence of a catalytic amount of TMSOTf in nitromethane