195192-23-5

Upstream product

• 132032-75-8 methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 359765-41-6 methyl 4-O-benzyl-7-deoxy-2,3-O-isopropylidene-7-(phenyldimethyl)silyl-L-glycero-α-D-manno-heptofuranoside 

Downstream Products

• 316364-86-0 (3aS,4R,7R,8aR,8bR)-7-((3aS,4S,6S,7R,7aS)-7-Benzyloxy-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-2,2-dimethyl-hexahydro-1,3,6-trioxa-5a-aza-as-indacen-4-ol 
• 195192-25-7 (3aS,4S,6R,7R,7aS)-7-Benzyloxy-6-((R)-1,2-bis-benzyloxy-ethyl)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 316364-87-1 (3aR,4R,7R,7aS)-7-Acetoxy-4-[(R)-2-((3aS,4S,6R,7R,7aS)-7-benzyloxy-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-2-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester 
• 316364-88-2 (3aR,4R,7R,7aS)-7-Acetoxy-4-[2-((3aS,4S,6R,7R,7aS)-7-benzyloxy-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester 
• 132032-81-6 methyl 4-O-benzyl-2,3-isopropylidene-L-glycero-α-D-manno-heptopyranoside 
• 195192-24-6 methyl 4-O-benzyl-2,3-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.

Synthesis of aza-C-disaccharides using cycloaddition reactions of a functionalized cyclic nitrone

Cycloaddition reactions of a functionalized nitrone with sugar alkenes gives stereoselective access to aza-C-disaccharide analogues of α-D-Lyx(1→6)-α-D-Man and →-D-Lyx(1→6)-D-Gal.

Synthesis of a trisaccharide fragment corresponding to the lipopolysaccharide region of vibrio parahaemolyticus

Vicinal syn-dihydroxylation of D-manno-hept-6-enopyranosides 4 and 10 with OsO4 afforded D-glycero-α-D-manno-heptopyranosides 5 and 11, respectively, in good yield and with a high degree of stereoselectivity. Compound 5 was converted into DD-He