18929-69-6

Upstream product

• 52290-47-8 methyl 6-bromo-6-deoxy-α-d-galactopyranoside triacetate 
• 98-88-4 benzoyl chloride 
• 52109-83-8 methyl 6-azido-6-deoxy-2,3,4-tri-O-acetyl-α-D-galactopyranoside 

Downstream Products

• 95908-43-3 2D-2,3/4,5-2,3,4-tribenzoyloxy-5-hydroxycyclohexanone 
• 95664-67-8 methyl 2,3,4-tri-O-benzoyl-6-deoxy-β-L-arabino-hex-5-enopyranoside 

Relevant academic research and scientific papers

Single diastereomers of polyhydroxylated 9-Oxa-1-azabicyclo[4.2.1]nonanes from intramolecular 1,3-dipolar cycloaddition of ω-unsaturated nitrones

8-Benzyloxymethyl-3,4,5-tribenzoyloxy-9-oxa-1-azabicyclo[4.2.1]nonane has been prepared as the single diastereoisomer 8 from an intramolecular 1,3-dipolar cycloaddition involving 2-(benzyloxy)acetaldehyde and ω-unsaturated hydroxylamine 7 derived from methyl α-D-glucopyranoside. The analogous 8-methoxycarbonyl 9-oxa-1-azabicyclo[4.2.1]nonane was afforded in a similar manner, from methyl D-galactopyranoside and methyl glyoxylate, as a 3:1 mixture of diastereoisomers 15 and 16. When conducted in achiral ionic liquid 17 this ratio increased to 8:1, and in chiral ionic liquid 18, compound 15 was formed exclusively.

Dioxolanylium Ions Derived from Carbohydrates. IX. Rearrangement between Dioxolanylium and Dioxanylium Ions

The formation of 4,6-acetoxonium and benzoxonium ion derivatives of methyl gluco-, manno-, galacto- and idopyranosides from the 6-azido-6-deoxy compounds on treatment with nitrosonium ion is described and the formation and rearrangement of the 3,5-benzoxonium ion derived from methyl α-d-xylofuranoside discussed.