359765-18-7

Upstream product

• 3970-20-5 allyl chloromethyl ether 
• 201788-59-2 methyl 5-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,4-furanoside 

Downstream Products

• 359765-20-1 methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside 
• 359765-22-3 (2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde 
• 359765-21-2 methyl 5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside 

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.