104486-80-8

Basic information

• Product Name: 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose
• CAS NO: 104486-80-8
• Molecular Weight: 462.408
• Mol File: 104486-80-8.mol

Chemical Properties

• CAS DataBase Reference: 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose(104486-80-8)
• EPA Substance Registry System: 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose(104486-80-8)

Safety Data

• Hazardous Substances Data: 104486-80-8(Hazardous Substances Data)

Usage

Type of compound

Chemical compound

Derivative of

Mannose (a type of sugar)

Structure

Contains six acetyl groups attached to the mannose molecule

Alteration of properties

The acetyl groups can change the chemical and biological properties of the compound

Common use

Research and pharmaceutical applications

Therapeutic properties

Potential anti-inflammatory and anti-cancer effects

Utilization

Synthesis of complex carbohydrates and glycoconjugates for biomedical studies

Importance

Has potential applications in medicine, biochemistry, and molecular biology

Upstream product

• 77533-48-3 Hexa-O-acetyl-α-D-glycero-L-gluco-heptopyranose 
• 108-24-7 acetic anhydride 
• 6946-17-4 6d-glycero-2,3,4,5-D-galacto-heptose 
• 1238399-48-8 C₈H₁₆O₇ 
• 6946-17-4 L-glycero-D-manno-heptose 
• 130272-67-2 L-glycero-D-manno-heptose 
• 127642-33-5 methyl L-glycero-α-D-manno-heptopyranoside 
• 122622-12-2 methyl 2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranoside 
• 64-19-7 acetic acid 
• 104430-49-1 2,3,4,5,6-Penta-O-acetyl-7-O-pivaloyl-D-glycero-D-galacto-heptose-trimethylendithioacetal 
• 1883-14-3 D-glycero-L-manno-heptose 
• 23102-92-3 D-glycero-L-gluco-heptose 
• 127-09-3 sodium acetate 
• 10589-31-8 D-glycero-D-altro-heptose 

Downstream Products

• 77533-48-3 Hexa-O-acetyl-β-D-glycero-L-gluco-heptopyranose 
• 5329-52-2 methyl-(penta-O-acetyl-α-D-glycero-L-gluco-heptopyranoside) 
• 131289-47-9 methyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-L-glycero-α-D-manno-heptopyranoside 
• 131316-89-7 methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside 
• 126456-55-1 1,2-O-(1-methoxy)ethylidene-3,4,6,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose 
• 116302-70-6 2-O-Acetyl-3,4,6,7-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranosylchlorid 
• 155786-55-3 allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-α-D-glucopyranoside 
• 155786-65-5 C₆₇H₆₈O₂₇ 
• 142270-29-9 1,2,3,4,6,7-hexa-O-benzoyl-L-glycero-α-D-manno-heptopyranose 
• 52571-89-8 Methyl-β-D-glycero-L-gluco-heptopyranosid 

Relevant articles and documents

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.

The inhibition of liposaccharide heptosyltransferase WaaC with multivalent glycosylated fullerenes: A new mode of glycosyltransferase inhibition

l,d-Heptosides (L-glycero-D-manno-heptopyranoses) are found in important bacterial glycolipids such as lipopolysaccharide (LPS), the biosynthesis of which is targeted for the development of novel antibacterial agents. This work describes the synthesis of

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

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.

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.

SYNTHESE DER L-GLYCERO-D-MANNO-HEPTOSE

Chain extension of 2,3:5,6-di-O-isopropylidene-D-manno-furanose 2 with 2-lithio-1,3-dithiane gives stereoselectively a derivative of D-glycero-D-galacto-heptose 3.Conversion of the heptose 2 by reduction of the aldehydo function and oxidation of the 7-OH group yields the D-glycero-D-manno-heptose 18.