869476-26-6

Basic information

• Product Name: 2,3-di-O-benzyl-2,3-dihydroxypent-4-enal
• Synonyms: 2,3-di-O-benzyl-2,3-dihydroxypent-4-enal
• CAS NO: 869476-26-6
• Molecular Weight: 296.366
• Mol File: 869476-26-6.mol

Chemical Properties

• Boiling Point: 426.8±45.0 °C(Predicted)
• Density: 1.092±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2,3-di-O-benzyl-2,3-dihydroxypent-4-enal(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-di-O-benzyl-2,3-dihydroxypent-4-enal(869476-26-6)
• EPA Substance Registry System: 2,3-di-O-benzyl-2,3-dihydroxypent-4-enal(869476-26-6)

Safety Data

• Hazardous Substances Data: 869476-26-6(Hazardous Substances Data)

Upstream product

• 220509-10-4 methyl 2,3-Di-O-benzyl-D-xylofuranoside 
• 1824-96-0 methyl xylofuranoside 
• 87-72-9 D-Xylose 
• 1251531-62-0 C₃₉H₃₈O₅ 
• 612051-06-6 methyl 5-deoxy-5-iodo-α/β-D-xyloside 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 869476-25-5 methyl 2,3-di-O-benzyl-5-deoxy-5-iodo-D-xylofuranoside 

Downstream Products

• 869476-28-8 ethyl (2S,3R,4S,5S)-4,5-bis(benzyloxy)-3-hydroxy-2-vinylhept-6-enoate 

Relevant articles and documents

Galacto configured N-aminoaziridines: A new type of irreversible inhibitor of β-galactosidases

A new type of galactose mimetics has been synthesized following a straightforward synthetic approach based on cyclohexene olefin aziridination reactions directed by hydroxyl substituents. These enantiomerically pure galacto-configured N-aminoaziridines are potent irreversible inhibitors of Aspergillus oryzae and Escherichia coli β-galactosidases.

Synthesis of cyclophellitol, cyclophellitol aziridine, and their tagged derivatives

Cyclitol epoxides and aziridines are potent and selective irreversible inhibitors of retaining glycosidases. We have previously reported on our studies on the use of activity-based probes derived from cyclophellitol and from its aziridine analogue for activity-based profiling of retaining β-glucosidases in vitro, in situ, and in some examples also in vivo. In this work we disclose full details of the synthesis, purification, and analysis of a comprehensive panel of cyclophellitol analogues, all featuring the β-glucose configuration and designed as tools for selective inhibition and/or imaging of human acid glucosylceramidase (epoxides) or as broad-spectrum probes for retaining β-glucosidases (aziridines).

Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses: en route to fluorinated carbanucleosides

The synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses is described. The sequence involves an addition of PhSeCF2TMS to carbohydrate-derived aldehydes or their corresponding tert-butanesulfinylimines followed by a radical cyclization. Optimized conditions for the PhSeCF2TMS addition to α-chiral aldehydes have been disclosed and its unusual diastereoselectivity is discussed. Application of the sequence using Ellman's auxiliary allows a more direct access to 1-aminopentose analogues with a complete control of the pseudo-anomeric center configuration.

A short synthesis of (+)-cyclophellitol

A new synthesis of (+)-cyclophellitol, a potent β-glucosidase inhibitor, has been completed in nine steps from D-xylose. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 5-deoxy-5-iodo-xylofuranoside followed by a h