6946-18-5

Basic information

• Product Name: heptopyranose
• Synonyms: 6-(1,2-dihydroxyethyl)tetrahydropyran-2,3,4,5-tetrol
• CAS NO: 6946-18-5
• Molecular Formula: C₇H₁₄O₇
• Molecular Weight: 210.1819
• Mol File: 6946-18-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 504.3°C at 760 mmHg
• Flash Point: 258.8°C
• Density: 1.81g/cm³
• Vapor Pressure: 2.78E-12mmHg at 25°C
• Refractive Index: 1.669
• CAS DataBase Reference: heptopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: heptopyranose(6946-18-5)
• EPA Substance Registry System: heptopyranose(6946-18-5)

Safety Data

• Hazardous Substances Data: 6946-18-5(Hazardous Substances Data)

Upstream product

• 101164-64-1 7-O-Pivaloyl-D-glycero-D-galacto-heptose-trimethylendithioacetal 
• 106445-48-1 benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside 
• 105592-29-8 benzyl 2,3-O-isopropylidene-β-L-glycero-D-manno-heptofuranoside 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 101305-22-0 D-glycero-D-galacto-Heptose-trimethylendithioacetal 
• 105592-31-2 benzyl 5,6,7-tri-O-acetyl-2,3-O-isopropylidene-β-L-glycero-D-manno-heptofuranoside 
• 105592-36-7 benzyl (E)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside 
• 106445-44-7 benzyl 2,3,4-tri-O-benzyl-β-L-glycero-D-manno-heptopyranurononitrile 
• 106445-46-9 (S)-2-Amino-1-((2R,3S,4S,5S,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanol 
• 57783-76-3 benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 15548-45-5 (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 
• 77455-30-2 benzyl 6-O-triphenylmethyl-α-D-mannopyranoside 
• 102046-36-6 (2S,3S,4S,5S,6S)-3,4,5,6-tetrabenzyloxytetrahydropyran-2-carbaldehyde 

Downstream Products

• 56570-93-5 D-erythro-L-galacto-Octono-1,4-lactone 
• 6968-62-3 D-erythro-L-talo-Octano-1,4-lactone 
• 127642-33-5 methyl L-glycero-α-D-manno-heptopyranoside 
• 686299-10-5 methyl L-glycero-α-D-manno-heptopyranoside 
• 104486-80-8 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose 
• 101400-24-2 1,2,3,4,6,7-Hexa-O-acetyl-L-glycero-β-D-manno-heptopyranose 
• 1048026-73-8 1-(N,N-dibenzyl)amino-1-deoxy-α-D-gluco-hept-2-ulopyranose 
• 1048026-76-1 1-(N-benzyl)amino-1-deoxy-α-D-gluco-hept-2-ulopyranose 
• 1048026-82-9 1-(N-benzyloxycarbonylmethyl)amino-1-deoxy-α-D-gluco-hept-2-ulopyranose 
• 1048026-84-1 1-(N-(5S-benzyloxycarbonyl)amino-6-carboxypentyl)amino-1-deoxy-α-D-gluco-hept-2-ulopyranose 
• 56654-37-6 methyl D-glycero-α-D-guloheptofuranoside 
• 52571-81-0 methyl D-glycero-α-D-guloheptopyranoside 
• 5349-39-3 methyl D-glycero-β-D-guloheptopyranoside 
• 77533-48-3 Hexaacetyl-α-u. β-D-glycero-D-galactoheptopyranose 

Relevant articles and documents

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.

SYNTHESIS OF L-glycero-D-manno-HEPTOSE

The easily accessible benzyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (2) can be converted, in a highly stereoselective manner, by the two-step Tamao method to benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside (4a).

NEW SYNTHESES OF D- AND L-GLYCERO-D-MANNO-HEPTOSES

Three methods for the synthesis of the title compounds starting from benzyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (7) have been elaborated.Conversion of 7 into the cyanohydrin followed by reduction to give the amine and then deamination gave a derivative of L-glycero-D-manno-heptose in low yield.Condensation of 7 with 2-methylfuran gave two stereoisomeric 6-C-(2-methyl-5-furyl) derivatives.The preponderant stereoisomer was ozonised and then reduced to give a derivative of D-glycero-D-manno-heptose.Condensation of 7 with allyloxymethylmagnesium chloride gave derivatives of both heptoses in good yield and with an L-glycero-D-glycero ratio of 3.2:1.Deprotection of these derivatives gave the heptoses in high yield.