14274-90-9

Basic information

• Product Name: 1,6-Anhydro-β-D-gulopyranose
• Synonyms: 1,6-Anhydro-β-D-gulopyranose;β-Gulosan
• CAS NO: 14274-90-9
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.1406
• Mol File: 14274-90-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,6-Anhydro-β-D-gulopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Anhydro-β-D-gulopyranose(14274-90-9)
• EPA Substance Registry System: 1,6-Anhydro-β-D-gulopyranose(14274-90-9)

Safety Data

• Hazardous Substances Data: 14274-90-9(Hazardous Substances Data)

Usage

Chemical structure

A six-membered ring structure with a glycosidic bond.

Derivative

A derivative of glucose.

Natural occurrence

Found in mucins and glycoproteins.

Biosynthesis

An important intermediate in the biosynthesis of various naturally occurring carbohydrates.

Chemical synthesis

Used as a precursor in the chemical synthesis of complex molecules.

Industrial applications

Used as a building block in the production of pharmaceuticals and agrochemicals.

Potential applications

Development of new materials and as a research tool in the study of carbohydrate chemistry and biochemistry.

Upstream product

• 104477-43-2 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-gulopyranose 

Downstream Products

• 14661-13-3 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-gulopyranose 
• 33297-50-6 Tri-O-benzoyl-1,6-anhydro-β-D-gulopyranose 
• 50880-93-8 tris-O-(toluene-4-sulfonyl)-1,6-anhydro-β-D-gulopyranose 
• 39809-41-1 1,5-Anhydro-exo-2,3-O-benzyliden-β-D-ribofuranose 
• 39809-40-0 1,5-Anhydro-endo-2,3-O-benzyliden-β-D-ribofuranose 
• 77852-62-1 1,6-Anhydro-exo-2,3-O-benzyliden-β-D-ribo-hexopyranos-4-ulose 
• 81413-15-2 8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside 
• 81413-16-3 8-methoxycarbonyloctyl 3,6-di-O-acetyl-2,4-di-O-benzyl-β-D-glucopyranoside 
• 81413-14-1 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranosyl chloride 
• 81413-21-0 8-methoxycarbonyloctyl-2,4-di-O-benzyl-3,6-di-O-<2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl>-α-D-glucopyranoside 
• 81413-17-4 8-methoxycarbonyloctyl 2,4-di-O-benzyl-α-D-glucopyranoside 
• 5694-94-0 1,3-Dioxolan-2,4-dicarbonsaeure 
• 6322-07-2 D-gulono-1,4-lactone 
• 77942-69-9 1,6-Anhydro-exo-2,3-O-benzyliden-β-D-gulopyranose 

Relevant articles and documents

Cycloheptaamylose as a model for starch in the pyrolysis of polysaccharides

The pyrolysis of cycloheptaamylose has been studied as a model for starch. 1,6-Anhydro-β-D-glucopyranose (levoglucosan, LG, 7) and its furanose isomer are major products from vacuum pyrolysis at 280, 300, and 320°, with combined yields ranging from 38 to 50% of the substrate-dependent on temperature. Pyrolysis in methyl sulfoxide at 150° produced LG and glucose as well as gluco-oligosaccharides of d.p. up to 7, with both reducing and 1,6-anhydro end-groups. A mechanism is postulated in which the first step is the heterolytic scission of a glucosidic linkage to form a linear, seven-membered oligosaccharide having a glucosyl cation in place of the reducing end-group. The cation is stabilized either by intramolecular attack of O-6 on the C-1 cation or by intermolecular transglycosylation. The former product subsequently yields LG upon scission of a terminal glucosidic linkage. The pyrolysis of cycloheptaamylose has been studied as a model for starch. 1,6-Anhydro-β-D-glucopyranose (levoglucosan, LG, 7) and its furanose isomer are major products from vacuum pyrolysis at 280, 300, and 320°, with combined yields ranging from 38 to 50% of the substrate dependent on temperature. Pyrolysis in methyl sulfoxide at 150° produced LG and glucose as well as gluco-oligosaccharides of d.p. up to 7, with both reducing and 1,6-anhydro end-groups. A mechanism is postulated in which the first step is the heterolytic scission of a glucosidic linkage to form a linear, seven-membered oligosaccharide having a glucosyl cation in place of the reducing end-group. The cation is stabilized either by intramolecular attack of O-6 on the C-1 cation or by intermolecular transglycosylation. The former product subsequently yields LG upon scission of a terminal glucosidic linkage.

O-BENZYL PROTECTING GROUPS AS HYDROGEN DONORS IN CATALYTIC TRANSFER HYDROGENOLYSIS. SELECTIVE DEBENZYLATION OF 1,6-ANHYDRO HEXOSES.

O-benzyl protecting groups may act as hydrogen donors in heterogenous catalytic transfer hydrogenolysis.Hydrogenolysis of compunds 1 - 4 demonstrated that this hydrogen transfer occurs adjacent cis-disposed hydroxyl groups are present.