359772-62-6

Upstream product

• 145240-53-5 1,6-Anhydro-4-azido-2-O-benzyl-4-deoxy-β-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 33208-46-7 1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose 
• 359772-43-3 1,6-Anhydro-4-azido-2-O-benzyl-4-deoxy-3-O-tosyl-β-D-glucopyranose 

Downstream Products

• 475102-19-3 1,6-anhydro-2-O-benzyl-3,4-dideoxy-3,4-tosylepimino-β-D-allopyranose 

Relevant academic research and scientific papers

Preparation of N-nosyl-3,4-epimines derived from levoglucosan by sodium borohydride reduction

Starting from 1,6-anhydro-β-d-glucopyranose 1 (levoglucosan), N-o-nitrobenzenesulfonyl (nosyl) 3,4-epimino derivatives with d-allo, d-galacto, and d-talo configurations have been prepared via NaBH4 reduction of suitably substituted azido tosylates. The benefits and limitations of this method over the classical LiAlH4 reduction method are discussed.

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.