127642-33-5

Basic information

• Product Name: methyl L-glycero-α-D-manno-heptopyranoside
• CAS NO: 127642-33-5
• Molecular Weight: 224.211
• Mol File: 127642-33-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: methyl L-glycero-α-D-manno-heptopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl L-glycero-α-D-manno-heptopyranoside(127642-33-5)
• EPA Substance Registry System: methyl L-glycero-α-D-manno-heptopyranoside(127642-33-5)

Safety Data

• Hazardous Substances Data: 127642-33-5(Hazardous Substances Data)

Upstream product

• 40653-15-4 methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 
• 105592-29-8 benzyl 2,3-O-isopropylidene-β-L-glycero-D-manno-heptofuranoside 
• 122622-12-2 methyl 2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranoside 
• 1238399-48-8 C₈H₁₆O₇ 
• 67-56-1 methanol 
• 6946-17-4 L-glycero-D-manno-heptose 
• 155020-83-0 methyl (6R)-2,3,4-tri-O-benzyl-6-(2-thiazolyl)-α-D-mannopyranoside 
• 222628-88-8 methyl 7-O-(2-aminoethyl)phosphoryl-L-glycero-α-D-manno-heptopyranoside 
• 222628-83-3 methyl 6-O-(2-aminoethyl)phosphoryl-L-glycero-α-D-manno-heptopyranoside 
• 222628-96-8 methyl 4-O-(2-aminoethyl)phophoryl-L-glycero-α-D-manno-heptopyranoside 
• 122588-51-6 methyl-2,3,4-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside 
• 127588-70-9 (R)-2-(Isopropoxy-dimethyl-silanyl)-1-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethanol 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 104486-80-8 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose 
• 127588-75-4 C₄₈H₅₀O₁₆ 
• 1520094-78-3 methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-3-O-(4-oxopentanoyl)-6,7-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-L-glycero-α-D-manno-heptopyranoside 
• 1520094-77-2 methyl 2-O-benzoyl-3-O-(4-oxopentanoyl)-6,7-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-L-glycero-α-D-manno-heptopyranoside 
• 1520094-76-1 methyl 2-O-benzoyl-6,7-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-L-glycero-α-D-manno-heptopyranoside 
• 1520094-75-0 methyl 2,3-di-O-benzoyl-4-O-dibenzyloxyphosphoryl-6,7-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-L-glycero-α-D-manno-heptopyranoside 
• 1520095-00-4 methyl 2,3-di-O-benzoyl-L-glycero-α-D-manno-heptopyranoside4-O-phosphoric acid 
• 1520094-99-8 methyl 2,3-di-O-benzoyl-4-O-(dibenzyloxyphosphoryl)-L-glycero-α-D-manno-heptopyranoside 
• 1520094-80-7 methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside 
• 1520094-79-4 methyl 2,3-di-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-L-glycero-α-D-manno-heptopyranoside 

Relevant articles and documents

Studies of alkaline mediated phosphate migration in synthetic phosphoethanolamine L-glycero-D-manno-heptoside derivatives

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.

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

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.

Diastereoselectivity in the synthesis of D-glycero-D-aldoheptoses by 2-trimethylsilylthiazole homologation from hexodialdo-1,5-pyranose derivatives

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