869780-44-9

Upstream product

• 57783-73-0 methyl 3,4-di-O-benzyl-α-D-mannopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 79218-91-0 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-6-O-trityl-β-D-mannopyramose 
• 100-44-7 benzyl chloride 
• 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 
• 65877-18-1 methyl 4,6-O-benzylidene-2,3-O-(dibutyl-stannylidene)-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 173778-31-9 methyl 3,4-di-O-benzyl-6-deoxy-6-ethylthio-α-D-mannopyranoside 
• 869780-45-0 methyl 6-azido-3,4-di-O-benzyl-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 

Relevant academic research and scientific papers

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

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.