127642-33-5Relevant articles and documents
Studies of alkaline mediated phosphate migration in synthetic phosphoethanolamine L-glycero-D-manno-heptoside derivatives
Stewart, Andrea,Bernlind, Christian,Martin, Adele,Oscarson, Stefan,Richards, James C.,Schweda, Elke K. H.
, p. 193 - 202 (1998)
Synthetic 2-, 3-, 4- and 6-monophosphate derivatives of methyl α-D-mannopyranosides, the 4-, 6- and 7-monophosphate derivatives of methyl L-glycero-α-D-manno-heptopyranosides and the corresponding phosphoethanolamine derivatives and a 6,7-cyclic phosphate analogue of methyl L-glycero-α-D-manno-heptopyranoside were used to study phosphate migration and hydrolysis when subjected to strong alkaline conditions (4 M KOH, 120°C, 18 h). The resulting products were analyzed by 1H NMR spectroscopy and electrospray mass spectrometry. It was found that phosphate substituents were stable under these conditions and neither migration nor hydrolysis was observed except for the heptose 7-phosphate, which gave a substantial amount of phosphate hydrolysis. In phosphoethanolamine-substituted compounds migration to adjacent positions with concomitant loss of ethanolamine was found together with hydrolysis. Copyright (C) 1998 Elsevier Science Ltd.
Large-scale synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose
Stanetty, Christian,Baxendale, Ian R.
, p. 2718 - 2726 (2015/04/27)
The higher-carbon sugar L-glycero-D-manno-heptose is a major constituent of the inner core region of the lipopolysaccharide (LPS) of many Gram-negative bacteria. All preparative routes used to date require multiple steps, and scalability has been rarely addressed. Here a highly practical synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose by a simple four-step sequence starting from L-lyxose is disclosed. Only two recrystallisations are required and the process was demonstrated on a >100 mmol scale, yielding 41 g of the target compound. A practical synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose in four simple steps from L-lyxose is disclosed. The process requires only two recrystallisations and was demonstrated on a >100 mmol scale, allowing rapid access to this important bacterial sugar building block in a convenient storage form.
Crystal and molecular structure of methyl L-glycero-α-D-manno- heptopyranoside, and synthesis of 1→7 linked L-glycero-D-manno-heptobiose and its methyl α-glycoside
Artner, Daniel,Stanetty, Christian,Mereiter, Kurt,Zamyatina, Alla,Kosma, Paul
, p. 1739 - 1746 (2011/12/02)
Methyl L-glycero-α-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-H···O hydrogen bond network. As model compounds for the side chain domains of the inner core structure of bacterial lipopolysaccharide, L-glycero-α-D-manno-heptopyranosyl-(1→7)-L- glycero-D-manno-heptopyranose and the corresponding disaccharide methyl α-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 Zemplen deacetylation.
The mechanism of the reaction catalyzed by ADP-β-L-glycero-D-manno- heptose 6-epimerase
Read, Jay A.,Ahmed, Raef A.,Morrison, James P.,Coleman Jr., William G.,Tanner, Martin E.
, p. 8878 - 8879 (2007/10/03)
ADP-L-glycero-D-manno-heptose 6-epimerase (AGME, RfaD) is a bacterial enzyme that is involved in lipopolysaccharide biosynthesis and interconverts ADP-β-L-glycero-D-manno-heptose (ADP-L,D-Hep) with ADP-β-D-glycero-D-manno-heptose (ADP-D,D-Hep). AGME is kn
Diastereoselectivity in the synthesis of D-glycero-D-aldoheptoses by 2-trimethylsilylthiazole homologation from hexodialdo-1,5-pyranose derivatives
Khare,Sood,Aspinall
, p. 237 - 246 (2007/10/02)
An exploration of the synthesis of D-glycero-D-altro-heptose, a constitutent of O antigen chains in lipopolysaccharides from Campylobacter jejuni serotypes O:23 and O:36 led to a study of the 2-trimethylsilylthiazole homologation procedure for heptose syn
Synthesis of methyl 3-O-(α-D-glucopyranosyl)-7-O-(L-glycero-α-D-manno-heptopyranosyl)-L-glycero-α-D-manno-heptopyranoside
Garegg, Per J.,Oscarson, Stefan,Szoenyi, Maria
, p. 125 - 132 (2007/10/02)
The title trisaccharide glycoside, which is related to part of the core region of the lipopolysaccharide from Salmonella, and the disaccharide glycosides methyl 3-O-α-D-glucopyranosyl-L-glycero-α-D-manno-heptopyranoside and methyl 7-O-L-glycero-α-D-manno-heptopyranosyl-L-glycero-α-D-manno-heptopyranoside have been synthesised.Methyl 2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside, obtained via a one-carbon elongation at C-6 of methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside, was used as precursor both for the heptosyl donor and acceptor.
Synthesis of L-glycero-α-D-manno-heptopyranose-containing disaccharide derivatives of the Neisseria meningitidis dephosphorylated inner-core region
Boons, G. J. P. H.,Marel, G. A. van der,Poolman, J. T.,Boom, J. H. van
, p. 339 - 343 (2007/10/02)
Hydroxymethylation of correctly protected alkyl α-D-manno-hexodialdo-1,5-pyronosides with magnesium chloride affords the corresponding silane intermediated, the isopropoxydimethylsilyl group of which can be unmasked with h
