79218-91-0

Upstream product

• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 76-83-5 trityl chloride 
• 100-44-7 benzyl chloride 
• 29073-91-4 (3aS,5R,6S,7aS)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 
• 100-39-0 benzyl bromide 
• 79218-92-1 1,2-O-(1-methoxyethylidene)-6-O-trityl-β-D-mannopyranose 

Downstream Products

• 65827-57-8 1,2,6-tri-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranose 
• 79218-89-6 methyl 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranoside 
• 79218-88-5 methyl 2,6-di-O-acetyl-3,4-di-O-benzyl-β-D-mannopyranoside 
• 73045-75-7 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl chloride 
• 79218-74-9 methyl 3,4-di-O-benzyl-β-D-mannopyranoside 
• 65827-63-6 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2,3-diol 
• 79218-90-9 6-O-acetyl-3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 79218-86-3 methyl 2,6-di-O-<2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl>-3,4-di-O-benzyl-α-D-mannopyranoside 
• 173778-32-0 methyl 3,4-di-O-benzyl-6-O-pivaloyl-α-D-mannopyranoside 
• 869780-44-9 methyl 3,4-di-O-benzyl-6-O-tosyl-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 
• 173778-36-4 methyl 3,4-di-O-benzyl-2-O-(1-bromo-2-methoxy-2-propyl)-6-chloro-6-deoxy-α-D-mannopyranoside 
• 173778-31-9 methyl 3,4-di-O-benzyl-6-deoxy-6-ethylthio-α-D-mannopyranoside 
• 173778-33-1 methyl 3,4-di-O-benzyl-6-chloro-6-deoxy-α-D-mannopyranoside 

Relevant academic research and scientific papers

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.

SYNTHESIS OF A MODEL OF AN IMMER CHAIN OF CELL-WALL PROTEOHETEROGLYCAN ISOLATED FROM Piricularia oryzae: BRANCHED D-MANNOPENTAOSIDES

Efficient syntheses are described of the branched D-mannopentaosides methyl 2,6-di-O-(2-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-α-D-mannopyranoside and methyl 2,4-di-O-(2-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-α-D-mannopyranoside, starting from the gly