359765-34-7

Upstream product

• 132032-75-8 methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside 
• 3970-20-5 allyl chloromethyl ether 

Downstream Products

• 359765-35-8 methyl 7-O-allyl-4,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptopyranoside 
• 359765-38-1 methyl 4,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptopyranoside 
• 359765-39-2 (S)-Benzyloxy-((3aS,4S,6S,7R,7aS)-7-benzyloxy-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-acetaldehyde 

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.