Crystal and molecular structure of methyl l-glycero-¦Á-d-manno-heptopyranoside, and synthesis of 1? linked l-glycero-d-manno-heptobiose and its methyl ¦Á-glycoside

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• 作者：Daniel  ; Artner^a ; Christian  ; Stanetty^a ; Kurt  ; Mereiter^b ; Alla  ; Zamyatina^a ; Paul  ; Kosma^a ;   ; ^{paul.kosma@boku.ac.at}
• 关键词：Glycoside ; Lipopolysaccharide ; Heptose ; Crystal structure ; Glycosyl donor
• 刊名：Carbohydrate Research
• 出版年：2011
• 出版时间：27 September 2011
• 年：2011
• 卷：346
• 期：13
• 页码：1739-1746
• 全文大小：633 K

文摘

Methyl l-glycero-¦Á-d-manno-heptopyranoside was synthesized in good yield by a Fischer-type glycosylation of the heptopyranose with methanol in the presence of cation-exchange resin under reflux and microwave conditions, respectively. The compound crystallized from 2-propanol in an orthorhombic lattice of space group P2₁2₁2 showing a comparatively porous structure with a 2-dimensional O¨CH?O hydrogen bond network. As model compounds for the side chain domains of the inner core structure of bacterial lipopolysaccharide, l-glycero-¦Á-d-manno-heptopyranosyl-(1?)-l-glycero-d-manno-heptopyranose and the corresponding disaccharide methyl ¦Á-glycoside were prepared. The former compound was generated via glycosylation of a benzyl 5,6-dideoxy-hept-5-enofuranoside intermediate followed by catalytic osmylation and deprotection. The latter disaccharide was efficiently synthesized in good yield by a straightforward coupling of an acetylated N-phenyltrifluoroacetimidate heptopyranosyl donor to a methyl 2,3,4,6-tetra-O-acetyl heptopyranoside acceptor derivative followed by Zempl¨¦n deacetylation.