130272-67-2

Basic information

• Product Name: glycero-alpha-manno-heptopyranose
• Synonyms: glycero-alpha-manno-heptopyranose;L-glycero-alpha-D-manno-heptopyranose
• CAS NO: 130272-67-2
• Molecular Formula: C₇H₁₄O₇
• Molecular Weight: 210.18186
• Mol File: 130272-67-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 504.3°Cat760mmHg
• Flash Point: 258.8°C
• Appearance: /
• Density: 1.81g/cm³
• Vapor Pressure: 2.78E-12mmHg at 25°C
• Refractive Index: 1.669
• CAS DataBase Reference: glycero-alpha-manno-heptopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: glycero-alpha-manno-heptopyranose(130272-67-2)
• EPA Substance Registry System: glycero-alpha-manno-heptopyranose(130272-67-2)

Safety Data

• Hazardous Substances Data: 130272-67-2(Hazardous Substances Data)

Usage

Definition

ChEBI: An aldoheptose in pyranose cyclic form with L-glycero-alpha-D-manno stereochemistry.

InChI:InChI=1/C7H14O7/c8-1-2(9)6-4(11)3(10)5(12)7(13)14-6/h2-13H,1H2/t2-,3-,4-,5-,6+,7-/m0/s1

Upstream product

• 211231-08-2 Phosphoric acid mono-[(2S,3S,4S,5S,6R)-6-((S)-1,2-dihydroxy-ethyl)-4,5-dihydroxy-2-methoxy-tetrahydro-pyran-3-yl] ester 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 105592-29-8 benzyl 2,3-O-isopropylidene-β-L-glycero-D-manno-heptofuranoside 
• 101305-20-8 3,4;6,7-Di-O-isopropyliden-D-glycero-D-galacto-heptose-trimethylendithioacetal 
• 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

• 77533-48-3 Hexaacetyl-α-u. β-D-glycero-D-galactoheptopyranose 
• 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 

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).

Branched and Chain-extended Sugars, XXX.- Diastereoselective Synthesis of L-glycero-D-manno-Heptose, a Constituent of the Inner Core Region of Lipopolysaccharides

Reaction of 2,3;5,6-di-O-isopropylidene-D-mannofuranose (1) with 2-lithio-1,3-dithiane affords diastereoselectively the 3,4;6,7-di-O-isopropylidene-D-glycero-D-galacto-heptose trimethylene dithioacetal (3).Conversion of compound 3 by a sequence of steps gives the tri-O-isopropylidene-D-glycero-D-galacto-heptit 16 which is oxidized with 1,1'-(azodicarbonyl)-dipiperidine to give the tri-O-isopropylidene-L-glycero-D-manno-heptose 17.Finally, compound 17 is transferred via the acetate 19 into the L-glycero-D-manno-heptopyranose 18.