Tetrahedron Asymmetry p. 1503 - 1508 (2002)
Update date:2022-09-26
Topics:
Izquierdo, Isidoro
Plaza, Maria T.
Franco, Francisco
The readily available 3,4-di-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose 2 was straightforwardly transformed into 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose 4, after treatment under modified Garegg's conditions followed by reaction of the resulting 3,4-di-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-L-sorbopyranose 3 with sodium azide in DMF. Cleavage of the acetonide of 4 to afford 6 followed by regioselective O-tert-butyldiphenylsilylation at C(1)OH afforded 7. Hydrogenation of 7 proceeded with high stereoselectivity yielding 3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-D-mannitol 1, confirmed by its O-desilylation to 8. Compound 1 was subjected to different N-protection reactions to afford the corresponding N-allyl (1a), N-benzyl (1b), and N-tert-butyloxycarbonyl (1c) derivatives.
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