54202-65-2

Upstream product

• 54202-59-4 1,6-anhydro-3-azido-4-O-benzyl-3-deoxy-2-O-tosyl-β-D-glucopyranose 
• 54295-80-6 O⁴-benzyl-O²-methanesulfonyl-3-(4-nitro-benzoylamino)-β-D-1,6-anhydro-3-deoxy-glucopyranose 

Downstream Products

• 475102-20-6 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-tosylepimino-β-D-mannopyranose 
• 54202-68-5 O⁴-benzoyl-2,3-benzoylazanediyl-β-D-1,6-anhydro-2,3-dideoxy-mannopyranose 
• 648858-56-4 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2-iodo-3-(N-o-nitrobenzenesulfonylamino)-β-D-glucopyranose 
• 648858-53-1 1,6-anhydro-4-O-benzyl-2,3-dideoxy-4-fluoro-3-(N-2-nitrobenzene-1-sulfonamido)-β-D-glucopyranose 
• 648858-49-5 1,6-anhydro-4-O-benzyl-2,3-dideoxy-(N-o-nitrobenzenesulfonylepimino)-β-D-mannopyranose 

Relevant academic research and scientific papers

Utilization of nosylepimines of 1,6-anhydro-β-D-hexopyranoses for the preparation of halogenated aminosaccharides

The aziridine ring cleavage of N-nosylepimines 3 and 7 having D-allo and D-manno configurations with halides led regioselectively to N-o- nitrobenzenesulfonylated 2-halo-3-amino- and 3-halo-2-amino-2,3-dideoxy derivatives of 1,6-anhydro-β-D-glucopyranose

Aziridine ring cleavage by nucleophiles in epimino derivatives of 1,6-anhydro-β-D-hexopyranoses

The regioselectivity of aziridine ring cleavage by nucleophiles (Cl-, Br-, I-, N3-, HBr) in a series of N-tosyl- and N-benzylepimino derivatives of 1,6-anhydro-β-D-hexopyranoses of D-allo, D-manno and D-galacto configurations has been studied. On treatment with halide anions, the tosylepimines 1, 3, 5 and 7 were opened trans-diaxially according to the Fuerst-Plattner rule. The courses of the reactions of benzylepimines 2, 4, 6 and 8 depended strongly on the configuration of the epimine and partially on the type of nucleophile used. On treatment with bromide and iodide, N-benzylepimines of D-allo (compounds 2, 4) and D-galacto (compound 6) configuration gave products of trans-diequatorial cleavage, while the manno-epimine 8 was opened trans-diaxially. In comparison, the reactions of all benzylepimines with azide and hydrobromic acid were independent of the configuration and proceeded trans-diaxially. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Synthesis and NMR spectra of 1,6-anhydro-2,3-dideoxy-2,3-epimino- and 1,6-anhydro-3,4-dideoxy-3,4-epimino-β-D-hexopyranoses

A complete series of 2,3-dideoxy-2,3-epimino-and 3,4-dideoxy-3,4-epimino-1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminum hydride reduction of the corresponding trans-azido tosylates or trans-azido epoxides of 1,6-anhydro-β-D-hexopyranoses. The structure of the epimino derivatives was confirmed by 1H and 13C NMR spectra.