223782-82-9

Upstream product

• 50692-26-7 2-O-isopropylidene-3-O-methoxymethyl-α-D-allofuranose 
• 100-39-0 benzyl bromide 
• 7757-38-2 2,3:5,6-di-O-isopropylidene-D-mannofuranose 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-L-gulonolactone 
• 3587-60-8 Benzyloxymethyl chloride 
• 33985-40-9 1-O-methyl-2,3-O-isopropylidene-α-D-mannopentoaldo-1,4-furanose 

Downstream Products

• 403501-59-7 methyl 6-O-benzyl-2,3-O-isopropylidene-5-O-methanesulfonyl-β-L-gulofuranoside 

Relevant academic research and scientific papers

Bicyclic diazasugars. Part 3: β-D-Mannose and 6-deoxy-β-L-gulose analogues

A bicyclic analogue of β-D-mannopyranose with nitrogen atoms replacing the ring and glycosidic oxygen atoms has been prepared in a single step from 5-O-mesyl-D-mannofuranose by a process that likely involves double displacement and an epoxide intermediate. A similar but protected bicyclic analogue of 6-deoxy-β-L-gulopyranose has been prepared by an electrophilic cyclization reaction.

Elongation of the pentose chain at the terminal carbon atom with Grignard C1 reagents. A study of the homologation reaction

Derivatives of four stereoisomeric pentodialdo-1,4-furanoses were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Derivatives of the expected stereoisomeric hexoses were accompanied in some cases by C-4 inverted products. The results have been discussed in terms of α- and β-chelated transition states. It has been found that the RX (X=O,Si) grouping of the Grignard reagent strongly influences the stereochemical outcome of the elongation reaction.