686299-10-5

Basic information

• Product Name: Heptopyranoside, methyl (9CI)
• Synonyms: Heptopyranoside, methyl (9CI)
• CAS NO: 686299-10-5
• Molecular Formula: C8H16O7
• Molecular Weight: 0
• Product Categories: ALCOHOL
• Mol File: 686299-10-5.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Heptopyranoside, methyl (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Heptopyranoside, methyl (9CI)(686299-10-5)
• EPA Substance Registry System: Heptopyranoside, methyl (9CI)(686299-10-5)

Safety Data

• Hazardous Substances Data: 686299-10-5(Hazardous Substances Data)

Upstream product

• 116302-67-1 penta-O-acetyl-α-D-glycero-D-galacto-heptopyranosyl bromide 
• 173010-21-4 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-((S)-1,2-diacetoxy-ethyl)-6-methoxy-tetrahydro-pyran-3-yl ester 
• 105592-29-8 benzyl 2,3-O-isopropylidene-β-L-glycero-D-manno-heptofuranoside 
• 1238399-48-8 C₈H₁₆O₇ 
• 67-56-1 methanol 
• 6946-17-4 L-glycero-D-manno-heptose 
• 22277-65-2 Methyl mannoside 
• 122622-12-2 methyl 2,3,4,6,7-penta-O-acetyl-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 
• 40653-15-4 methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 
• 122588-51-6 methyl-2,3,4-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside 
• 103597-24-6 methyl 2,3,4-tri-O-benzyl-L-glycero-α-D-gluco-heptopyranoside 
• 134680-55-0 methyl 2,3,4-tri-O-benzyl-α-D-galacto-hexodialdo-1,5-pyranoside 

Downstream Products

• 127642-33-5 methyl L-glycero-α-D-manno-heptopyranoside 

Relevant articles and documents

Convenient synthesis of methyl L-Glycero-D-Manno-heptopyranoside

Methyl L-glycero-D-manno-heptoside was prepared from a butane diacetal (BDA) derivative of methyl mannoside. Benzylation of the 3,4-BDA mannoside gave the 2-benzyl ether as a major product, which eliminated blocking and deblocking of the primary hydroxy g

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.

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.