79218-74-9

Upstream product

• 2774-19-8 (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 79218-89-6 methyl 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranoside 
• 73395-14-9 methyl (R,R)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 100-44-7 benzyl chloride 
• 86172-79-4 (2S,3S,4S,5R,6R)-2-Methoxy-4-trityloxy-6-trityloxymethyl-tetrahydro-pyran-3,5-diol 
• 86172-78-3 (2R,3S,4S,5S,6S)-6-Methoxy-5-trityloxy-2-trityloxymethyl-tetrahydro-pyran-3,4-diol 
• 194149-26-3 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 22277-65-2 Methyl mannoside 
• 4148-71-4 methyl exo-2,3:4,6-di-O-benzylidene-β-D-mannopyranoside 
• 2774-19-8 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 
• 29073-91-4 (3aS,5R,6S,7aS)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 
• 79218-92-1 1,2-O-(1-methoxyethylidene)-6-O-trityl-β-D-mannopyranose 

Downstream Products

• 79218-89-6 methyl 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranoside 
• 147985-39-5 methyl 3,4-di-O-benzyl-2,6-di-O-benzyl-2,6-di-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimino-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 173778-32-0 methyl 3,4-di-O-benzyl-6-O-pivaloyl-α-D-mannopyranoside 
• 688799-98-6 methyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-D-mannopyranoside 
• 173778-31-9 methyl 3,4-di-O-benzyl-6-deoxy-6-ethylthio-α-D-mannopyranoside 
• 173778-36-4 methyl 3,4-di-O-benzyl-2-O-(1-bromo-2-methoxy-2-propyl)-6-chloro-6-deoxy-α-D-mannopyranoside 
• 173778-34-2 methyl 3,4-di-O-benzyl-2-(1-bromo-2-methoxy-2-propyl)-6-deoxy-6-(ethylthio)-α-D-mannopyranoside 
• 1361383-33-6 2,4-di-O-benzyl-6-deoxy-3-(2-naphthylmethyl)-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside) 
• 1361383-34-7 2,4-di-O-benzyl-6-deoxy-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside) 
• 125519-98-4 methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside 
• 145149-85-5 Methyl 3,4-di-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside 
• 15038-71-8 methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 50272-14-5 (2R,4aR,6S,7S,8aS)-7-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 

Relevant academic research and scientific papers

Mannose-binding geometry of pradimicin A

Pradimicins (PRMs) and benanomicins are the only family of non-peptidic natural products with lectin-like properties, that is, they recognize D-mannopyranoside (Man) in the presence of Ca2+ ions. Coupled with their unique Man binding ability, t

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

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

Synthesis of novel mannose-based crown ethers

A novel class of chiral crown ether analogues incorporating carbohydrate subunits can be easily prepared from methyl α-D-mannopyranoside. By a short reaction sequence involving either alkylations using a dibutylstannane intermediate or by phase transfer c

Borane/Bu2BOTf: A mild reagent for the regioselective reductive ring opening of benzylidene acetals in carbohydrates

BH3/Bu2OTf is an effective reagent to reductively cleave 4,6-O-benzylidene acetals of various hexopyranosides to the corresponding 4-O-benzyl ethers. 4,6-O-Isopropylidene acetals can be similarly cleaved. Common protecting groups are

Chemistry of 1-alkoxy-1-glycosyl radicals: The manno- and rhamnopyranosyl series. Inversion of α- to β-pyranosides and the fragmentation of anomeric radicals

The formation and stereoselective quenching of 1-mannopyranosyl radicals by a tributyltin hydride-mediated intramolecular 1,5-hydrogen abstraction sequence is described. A competing process is 1,4-hydrogen atom abstraction leading principally to glucopyran-2-ulosides. Fragmentation of the anomeric radical resulting in the formation of ring opened products is a problem in certain series. The chemistry is dictated to a considerable extent by the nature of the protecting groups employed with the 4,6-benzylidene series and, for rhamnose, the Ley 3,4-dispiroketal, being particularly susceptible to the 1,4-hydrogen atom abstraction but less to the fragmentation. Photochemical conditions are described, in which these side reactions are practically eliminated, and applied to the inversion of an α- to a β-mannoside in a disaccharide.

Control of glycoprotein synthesis. Characterization of (1->4)-N-acetyl-β-D-glucosaminyltransferases acting on the α-D-(1->3)- and α-D-(1->6)-linked arms of N-linked oligosaccharides

Hen oviduct membranes contain at least three N-acetyl-β-D-glucosaminyltransferases (GlcNAc-T) that attach a βGlcNAc residue in (1-4)-linkage to a D-Manp residue of the N-linked oligosaccharide core, i.e., (1->4)-β-D-GlcNAc-T III which adds a "bisecting " GlcNAc group to form the β-D-GlcpNAc-(1->4)-β-D-Manp-(1->4)-D-GlcNAc moiety: (1->2)-β-D-GlcNAc-T IV which adds a GlcNAc group to the (1->3)-α-D-Man arm to form the β-D-GlcpNAc-(1->4)-2)>-α-D-Manp-(1->3)-β-D-Manp-(1->4)-D-GlcpNAc component; and (1->4)-β-D-GlcNAc-T VI which adds a GlcNAc group to the α-D-Manp residue of β-D-GlcpNAc-(1->6)-2)>-α-D-Manp-R to form β-D-GlcpNAc-(1->6)-4)>-2)>-α-D-Manp-R.We now report a novel (1->4)-β-D-GlcNAc-T activity (GlcNAc-T VI') in hen oviduct membranes that transfers GlcNAc to β-D-GlcpNAc-(1->2)-α-D-Manp-(1->6)-β-D-Manp-R to form β-D-GlcpNAc-(1->4)-2)>-α-D-Manp-(1->6)-β-D-Manp-R.The structure of the enzyme product was confirmed by 1H NMR spectroscopy.FAB-mass spectrometry and methylation analysis.Previous work with GlcNAc-T IV was carried out with biantennary substrates; we now show that hen oviduct membrane GlcNAc-T IV can also transfer GlcNAc to monoantennary β-D-GlcpNAc-(1->2)-α-D-Manp-(1->3)-β-D-Manp-R to form β-D-GlcpNAc-(1->4)-2)>-α-D-Man-p-(1->3)-β-D-Manp-R.The findings that GlcNAc-T VI'and IV have similar kinetic characteristics and that hen oviduct membranes can convert methyl β-D-GlcpNAc-(1->2)-α-D-Manp to methyl β-D-GlcpNAc-(1->4)-2)>-α-D-Manp suggest that these two activities may be due to the same enzyme.The R-group of the β-D-GlcpNAc-(1->2)-α-D-Manp-(1->6)-β-D-Manp (or Glcp)-R substrate has an important influence on GlcNAc-T VI'enzyme activity.When R is GlcNAc or βGlc-ally, the activity is drastically reduced.This may be due to conformational factors and may explain why hen oviduct membranes add a GlcNAc residue in (1->4)-β-linkage mainly to the (1->3)-α-D-Man arm of the bi-antennary substrate β-D-GlcpNAc-(1->2)-α-D-Manp-(1->6)-2)-α-D-Manp-(1->3)>-β-D-Manp-R to form β-D-GlcpNAc-(1->2)-α-D-Manp-(1->6)-2)-4)>-α-D-Manp-(1->3)>-β-D-Manp-R.

SYNTHESIS OF EVERNINOSE, A NON-REDUCING DISACCHARIDE COMPONENT OF THE ORTHOSOMYCIN-TYPE OLIGOSACCHARIDE ANTIBIOTICS

Glycosylation of 3,4-di-O-benzyl-2-O-methyl-L-lyxopyranose (1) with 3,4-di-O-benzyl-2,6-di-O-methyl-α-D-mannopyranosyl chloride afforded a mixture of the α,α- 12) and α,β-disaccharide derivative (10).Reaction of 1 with 3,4-di-O-benzyl-2,6-di-O-methyl-α-D-