359765-39-2

Upstream product

• 132032-75-8 methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside 
• 359765-35-8 methyl 7-O-allyl-4,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptopyranoside 
• 359765-34-7 methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero and D-glycero-α-D-manno-heptopyranosides 
• 100-39-0 benzyl bromide 
• 359765-38-1 methyl 4,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptopyranoside 

Relevant academic research and scientific papers

From methyl mannosides to methyl octosides by a stepwise homologation with Grignard C1 reagents

A four-step procedure for homologation of methyl α-D-manno furanoside and α-D-manno pyranoside was examined. The reactions consisted in (i) oxidation of the terminal hydroxymethyl group in a protected sugar derivative to an aldehyde; (ii) reaction with allyloxymethylmagnesium chloride (or (phenyldimethyl)silylmethyl-magnesium chloride); (iii) protection of the newly formed secondary alcohol group; (iv) deprotection of the terminal CH2OR (or oxidation of the CH2SiMe2Ph) group. From methyl α-D-mannosides, stereoisomeric DαD and LαD methyl heptosides and from them, methyl octosides of D-threo- and L-erythro-α-D-manno configuration were obtained.