60885-00-9

Basic information

• Product Name: 1-O-benzyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
• Synonyms: 1-O-benzyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
• CAS NO: 60885-00-9
• Molecular Weight: 350.412
• Mol File: 60885-00-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-O-benzyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-benzyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose(60885-00-9)
• EPA Substance Registry System: 1-O-benzyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose(60885-00-9)

Safety Data

• Hazardous Substances Data: 60885-00-9(Hazardous Substances Data)

Upstream product

• 20880-92-6 2,3;4,5-di-O-isopropylidene-β-D-fructopyranose 
• 100-44-7 benzyl chloride 
• 470-23-5 D-fructose 
• 100-39-0 benzyl bromide 

Downstream Products

• 575472-02-5 1-O-benzyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine 
• 198215-77-9 4,5-di-O-benzoyl-2,3-O-((1S*)-1-benzyloxymethylethylidene)-β-D-fructopyranose 
• 198215-76-8 4,5-di-O-benzoyl-2,3-O-((1R*)-1-benzyloxymethylethylidene)-β-D-fructopyranose 
• 198215-71-3 4,5-di-O-benzoyl-1-O-benzyl-2,3-O-isopropylidene-β-D-fructopyranose 
• 152192-23-9 (S)-2,3-O-(1-methylethylidene)-1-O-phenylmethyl-4,5-O-sulfinyl-β-D-fructopyranose 
• 152192-24-0 (R)-2,3-O-(1-methylethylidene)-1-O-phenylmethyl-4,5-O-sulfinyl-β-D-fructopyranose 
• 205249-00-9 (3aS,5aR,8aR,8bS)-3a-Benzyloxymethyl-2,2-dimethyl-7,7-bis-trifluoromethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 205249-27-0 (3aS,5aR,8aR,8bS)-3a-Benzyloxymethyl-2,2-dimethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-7-thione 
• 205249-23-6 (3aS,5aR,9aR,9bS)-3a-Benzyloxymethyl-2,2-dimethyl-hexahydro-1,3,4,6,9-pentaoxa-cyclopenta[a]naphthalene 
• 205248-90-4 (3aS,5aR,8aR,8bS)-3a-Benzyloxymethyl-2,2-dimethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 205249-07-6 (1aS,3aS,6aS,6bR)-3a-Benzyloxymethyl-1,1-dichloro-5,5-dimethyl-hexahydro-3,4,6-trioxa-cyclopropa[e]indene 
• 205248-98-2 (3aS,6S,7S,7aS)-3a-Benzyloxymethyl-6-chloro-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-ol 
• 205248-99-3 (1aR,3aS,6aS,6bR)-3a-Benzyloxymethyl-5,5-dimethyl-tetrahydro-1,3,4,6-tetraoxa-cyclopropa[e]indene 
• 205249-39-4 (3aS,7aS)-3a-Benzyloxymethyl-2,2-dimethyl-5,7a-dihydro-3aH-[1,3]dioxolo[4,5-b]pyran 

Relevant articles and documents

Inhibition of the D-fructose transporter protein GLUT5 by fused-ring glyco-1,3-oxazolidin-2-thiones and -oxazolidin-2-ones

The glucose transporter 5 (GLUT5) - a specific D-fructose transporter - belongs to a family of facilitating sugar transporters recently enlarged by the human genome sequencing. Prompted by the need to develop specific photolabels of these isoforms, we have studied the interaction of conformationally locked D-fructose and L-sorbose derived 1,3-oxazolidin-2-thiones and 1,3-oxazolidin-2-ones to provide a rational basis for an interaction model. The inhibition properties of the D-fructose transporter GLUT5 by glyco-1,3-oxazolidin-2-thiones and glyco-1,3-oxazolidin-2-ones is now reported. In vitro, the fused-rings systems tested showed an efficient inhibition of GLUT5, thus bringing new insights on the interaction of D-fructose with GLUT5.

Synthesis of hydroxylated derivatives of topiramate, a novel antiepileptic drug based on D-fructose: Investigation of oxidative metabolites

To corroborate the structures of two monohydroxylated metabolites of topiramate (1), we synthesized four monosaccharide derivatives from D- fructose: 4,5-O-[(1R*)- and 4,5-O-[(1S*)-1-hydroxymethylethylidene]-2,3-O- isopropylidene-β-D-fructopyranose sulfamates (2a and 2b); 2,3-O-[(1R*)- and 2,3-O-[(1R*)-1-hydroxymethylethylidene]-4,5-O-isopropylidene-β-D- fructopyranose sulfamates (3a and 3b). The route to 2a and 2b was brief and straightforward, while that to 3a and 3b was more involved. In the latter case, the D-fructose bis-acetal 10 was benzylated and converted to a monoacetal dibenzoate (14) (50% yield), which was then transacetalized to give a mixture of 4,5-dibenzoyl-2,3-O-[(1R* and 4,5-dibenzoyl-2,3-O-[(1S*)- 1-benzyloxymethylethylidene]-β-D-fructopyranose (16a and 16b) (22%). The individual diastereomers were separated and processed via ester saponification, acetonation, sulfamoylation, and hydrogenolysis into 3a (36%) and 3b (27%). Structure 2b was confirmed for one oxidative metabolite, but the other metabolite was found not to correspond with either 2a, 3a, or 3b. On the basis of CI-MS and 1H NMR data, a (2-hydroxy-1,4-dioxano)pyran structure, 4, is proposed for this unidentified metabolite.