106444-74-0

Upstream product

• 73395-14-9 methyl (R,R)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 872352-57-3 methyl 3-O-allyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranoside 
• 67381-27-5 methyl 3-O-allyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 15038-71-8 methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 106499-04-1 methyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 58341-56-3 methyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 82228-10-2 methyl 3-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 106444-77-3 8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide 
• 106444-76-2 8-methoxycarbonyloctyl-6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl bromide 
• 86861-45-2 1,6-Di-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranose 
• 83259-13-6 6-O-acetyl-3-O-allyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide 
• 211231-18-4 (S)-1-((2R,3S,4S,5S,6S)-4-Allyloxy-3,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethanol 
• 211231-34-4 3-[(2R,3R,4S,5S,6S)-3,5-Bis-benzyloxy-2-((S)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide 
• 211231-19-5 (2R,3S,4S,5S,6S)-4-Allyloxy-3,5-bis-benzyloxy-2-((S)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran 
• 211231-20-8 (2R,3S,4S,5S,6S)-3,5-Bis-benzyloxy-2-((S)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-ol 
• 126412-69-9 methyl 3-O-allyl-2,4-di-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 
• 154918-95-3 methyl 3-O-allyl-2,4-di-O-benzyl-6-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)-α-D-mannopyranoside 

Relevant academic research and scientific papers

Nucleofuge Generating Glycosidations by the Remote Activation of Hydroxybenzotriazolyl Glycosides

Hydroxybenzotriazole is routinely used in peptide chemistry for reducing racemization due to the increased reactivity. In this article, very stable hydroxybenzotriazolyl glucosides were identified to undergo glycosidation. The reaction was hypothesized to go through the remote activation by the Tf2O at the N3-site of HOBt followed by the extrusion of the oxocarbenium ion that was attacked by the glycosyl acceptor. Further, equilibration of the zwitterionic benzotriazolyl species makes the leaving group noncompetitive and generates the nucleofuge that has been reconverted to the glycosyl donor. The reaction is mild, high yielding, fast and suitable for donors containing both C2-ethers and C2-esters as well. The regenerative-donor glycosidation strategy is promising as it enables us to regenerate the glycosyl donor for further utilization. The utility of the methodology for the oligosaccharide synthesis was demonstrated by the successful synthesis of the branched pentamannan core of the HIV1-gp120 complex.

Substrates for the differentiation of the N-acetylglucosaminyltransferases. Synthesis of βDGlcNAc(->2)αDMan(1->6)βDMan and βDGlcNAc(1->2)αDMan(1->6)3)βDMan glycosides

The trisaccharide βDGlcNAc(1->2)αDMan(1->6)βDMan (2) and the tetrasaccharide βDGlcNAc(1->2)αDMan(1->6)αDMan(1->3)>βDMan (3) have been chemically synthesized as their 8-methoxycarbonyloctyl glycosides.Compounds 2 and 3, both partial structures of naturally