52571-86-5

Upstream product

• 287477-93-4 Methyl 2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-galacto-heptopyranoside 
• 321142-29-4 methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-galacto-heptopyranoside 
• 321142-25-0 methyl 2,3,4,7-tetra-O-benzyl-D-glycero-α-D-galacto-heptopyranoside 
• 287396-53-6 Methyl 2,3,4-tri-O-acetyl-7-O-allyl-D-glycero-α-D-galacto-heptopyranoside 
• 134680-55-0 methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside 

Relevant academic research and scientific papers

Homologation of protected hexoses with Grignard C1 reagents

Derivatives of three stereoisomeric hexodialdo-1,5-pyranosides were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Two stereoisomeric heptoses were obtained in each case in a good yield. The methyl alloside-derived heptosides were accompanied by C-5 inverted products. The addition of Grignard reagents to aldehydes 5-8 has been discussed in terms of parallel α- or β-chelated and Felkin-Anh transition states. It has been found that the silyl Grignard reagent 12 exhibits a strong preference for the formation of heptose derivatives of L-configuration at C-6. (C) 2000 Elsevier Science Ltd.

Homologation of ?-acetylated methyl hexopyranosides with a Grignard C1 reagent

Three methyl 2,3,4-tri-?-acetyl-α-D-hexopyranosides of the manno, gluco, and galacto configuration were oxidized to the corresponding methyl hexodialdo-1,5-pyranosides and then reacted with allyloxymethylmagnesium chloride. Methyl heptopyranosides of the D-and L-glycero-α-D-manno-, -α-D-gluco, and -α-D-galacto configuration were obtained in moderate yields. Migration of the 4-?-acetyl group in the products was observed. An interpretation of the results was proposed.