Record number :
961571
Title of article :
Synthesis of dibekacin analogs containing 3-oxaand 3-aza-2,3,4-trideoxy-d-glycero-hexopyranose
Author/Authors :
Ryuji Kuwahara، نويسنده , , Tsutomu Tsuchiya، نويسنده ,
Issue Information :
دوهفته نامه با شماره پیاپی سال 1996
Pages :
16
From page :
15
To page :
30
Abstract :
6-O-(3-Oxa-2,3,4-trideoxy-α-d-glycero-hexopyranosyl) derivatives (10 and 17) of both 3′,4′-dideoxyneamine and 5-epifluoro-5,3′,4′-trideoxyneamine have been prepared by coupling ethyl 6-O-benzyl-3-oxa-2,3,4-trideoxy-1-thio-d-glycero-hexopyranoside (5) with suitable aglycons. The corresponding 3″-aza derivative (19) of dibekacin (6) was prepared by oxidation of 1,3,2′,6′-tetra-N-tosyldibekacin (7) with Pb(OAc)4 followed by treatment with NH4OAc and reduction with NaBH3CN. Related ring-opening compounds (11 and 25) were also prepared.
Keywords :
5-Deoxy-5-fluorination , Aminoglycoside antibiotic , Pb(OAc)4 oxidation , Reductive amination , Na in liquid NH3 , Glycosylation
Journal title :
Carbohydrate Research
Link To Document :