686299-10-5

Upstream product

• 287477-93-4 Methyl 2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-galacto-heptopyranoside 
• 5329-52-2 methyl-(penta-O-acetyl-β-D-glycero-D-galacto-heptopyranoside) 
• 67-56-1 methanol 
• 3146-50-7 D-glycero-D-gulo-heptose 
• 6946-18-5 D-glycero-D-guloheptopyranose 
• 7647-01-0 hydrogenchloride 
• 5329-52-2 methyl-(penta-O-acetyl-α-D-glycero-L-gluco-heptopyranoside) 
• 109120-19-6 methyl-(penta-O-acetyl-α-D-glycero-L-manno-heptopyranoside) 
• 23102-92-3 D-glycero-L-gluco-heptose 
• 1883-14-3 D-glycero-L-manno-heptose 
• 321142-26-1 methyl 2,3,4,7-tetra-O-benzyl-L-glycero-α-D-galacto-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 
• 6946-17-4 L-glycero-D-manno-heptose 
• 1238399-48-8 C₈H₁₆O₇ 

Downstream Products

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

Relevant academic research and scientific papers

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

Large-scale synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose

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

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

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

Homologation of protected hexoses with Grignard C1 reagents

Derivatives of three stereoisomeric hexodialdo-1,5-pyranosides were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Two stereoisomeric heptoses were obtained in each case in a good yield. The methyl alloside-derived heptosides were accompanied by C-5 inverted products. The addition of Grignard reagents to aldehydes 5-8 has been discussed in terms of parallel α- or β-chelated and Felkin-Anh transition states. It has been found that the silyl Grignard reagent 12 exhibits a strong preference for the formation of heptose derivatives of L-configuration at C-6. (C) 2000 Elsevier Science Ltd.

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.

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.

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

Synthesis of methyl 3-O-(α-D-glucopyranosyl)-7-O-(L-glycero-α-D-manno-heptopyranosyl)-L-glycero-α-D-manno-heptopyranoside

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

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