86342-19-0

Upstream product

• 23392-29-2 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 67381-28-6 methyl 3,6-di-O-allyl-2,4-di-O-benzyl-α-D-mannopyranoside 
• 15038-71-8 methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 227306-95-8 methyl 2,4-di-O-benzyl-3,6-di-O-trityl-α-D-mannopyranoside 
• 73395-15-0 methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 73395-14-9 methyl (R,R)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 86172-79-4 (2S,3S,4S,5R,6R)-2-Methoxy-4-trityloxy-6-trityloxymethyl-tetrahydro-pyran-3,5-diol 
• 100-39-0 benzyl bromide 
• 194149-26-3 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 67-56-1 methanol 
• 67381-27-5 methyl 3-O-allyl-α-D-mannopyranoside 
• 872352-57-3 methyl 3-O-allyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranoside 
• 106444-74-0 methyl 2,4-di-O-benzyl-3-O-allyl-α-D-mannopyranoside 
• 15038-71-8 methyl 2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 

Downstream Products

• 80599-54-8 methyl 2,4-di-O-benzyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 79218-68-1 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 68601-72-9 methyl 2,4-di-O-benzyl-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→3))-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→6))-α-D-mannopyranoside 
• 79317-23-0 methyl 2,4-di-O-benzyl-6-O-(2,4-di-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 80738-51-8 Acetic acid (2R,3R,4S,5S,6S)-2-acetoxymethyl-3,5-bis-benzyloxy-6-((2R,3S,4S,5S,6S)-3,5-bis-benzyloxy-4-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester 
• 79218-64-7 C₆₉H₇₈O₂₀ 
• 78880-16-7 methyl 2,4-di-O-benzyl-6-O-(2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 154919-11-6 methyl 2,4-di-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 80738-49-4 methyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranoside 
• 79218-73-8 methyl 2,4-di-O-benzyl-6-O-trityl-α-D-mannopyranoside 
• 79218-72-7 methyl 2,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside 
• 79330-97-5 methyl 6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside 
• 493008-73-4 methyl 2,4-di-O-benzyl-3,6-di-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 80738-50-7 1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose 

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.

Gold-catalysed glycosylation reaction using an easily accessible leaving group

Gold(iii)-catalysed glycosylation reaction has been developed by employing a new and easily accessible leaving group synthesized from ethyl cyanoacetate. Several nucleophiles like alcohols, thiols, allyltrimethylsilane, trimethylsilyl azide and triethylsilane have been reacted to make the corresponding glycosides in good yields and with marginal to excellent α-selectivity. This journal is

β-Rhamnosides from 6-thio mannosides

Upon condensation of 6-thio-6-deoxy-mannosyl donors 1,2-cis products are obtained with a high degree of stereoselectivity. Subsequent reductive removal of the 6-thio functionality gives 1,2-cis rhamnosides. The 1,2-cis-selectivity can be rationalized with

Rapid assembly of gp120 oligosaccharide moieties via one-pot glycosidation-deprotection sequences

Mannosyl trihaloacetimidate donors equipped with a 2-O-Fmoc group can be effectively activated by catalytic Bi(OTf)3 in glycosidations. Despite the expected participating effect of the Fmoc group, the reaction solvent was found to be decisive f

One-pot catalytic glycosidation/Fmoc removal - An iterable sequence for straightforward assembly of oligosaccharides related to HIV gp120

The removal of a transient Fmoc protecting group can be simply performed by the addition of excess Et3N just after the accomplishment of a Bi(OTf)3-promoted glycosidation reaction. The obtained oligosaccharide can be directly employed as a glycosyl acceptor for further elongation of the saccharide. The preparation of biologically important, linear and branched mannans incorporated into HIV gp 120 demonstrates that the iteration of this one-pot sequence leads to a very straightforward oligosaccharide assembly.

Efficient synthesis of man2, man3, and man 5 oligosaccharides, using mannosyl iodide donors

A highly efficient protocol for making Man3 and Man5 oligosaccharides with use of orthogonally protected glycosyl iodide donors has been developed. Glycosylation of a C-2-O-acetyl mannosyl iodide donor in the presence of silver trifl

Glycosylation using a one-electron-transfer, homogeneous reagent. Application to an efficient synthesis of the trimannosyl core of N-glycosylproteins

Double glycosylation of methyl 2,4-di-O-benzyl-β-D-mannopyranoside with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside using as promoter tris(4-bromophenyl)ammoniumyl hexachloroantimonate, a stable, commercial, and crystalline radical cat