TY - JOUR
T1 - Synthesis of sialic acid analogues with the oxime group at C-4 or C-5 of KDN
AU - Kai, Toshitsugu
AU - Sun, Xue
AU - Takayanagi, Hiroaki
AU - Furuhata, Kimio
PY - 1997/1/1
Y1 - 1997/1/1
N2 - The readily available methyl (methyl 3-deoxy-5, 8 : 7,9-di-O-isopropylidene-β-D-glycero-D-galacto-2-nonulopyranosid)onate (7) was converted in five synthetic steps into methyl (methyl 4-acetamido-3, 4-dideoxy-β-D-glycero-D-talo-2-nonulopyranosid)onate (11). Selective protection of the C-4, C-7, C-8 and C-9 hydroxy groups of methyl (methyl 3-deoxy-8,9-O-isopropylidene-β-D-glycero-D-galacto-2-nonulpyranosid)onate (2) followed by oxidation of the C-5 hydroxy group and then its oximination gave 5-hydroxyimino derivatives (1 5 and 1 6).
AB - The readily available methyl (methyl 3-deoxy-5, 8 : 7,9-di-O-isopropylidene-β-D-glycero-D-galacto-2-nonulopyranosid)onate (7) was converted in five synthetic steps into methyl (methyl 4-acetamido-3, 4-dideoxy-β-D-glycero-D-talo-2-nonulopyranosid)onate (11). Selective protection of the C-4, C-7, C-8 and C-9 hydroxy groups of methyl (methyl 3-deoxy-8,9-O-isopropylidene-β-D-glycero-D-galacto-2-nonulpyranosid)onate (2) followed by oxidation of the C-5 hydroxy group and then its oximination gave 5-hydroxyimino derivatives (1 5 and 1 6).
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U2 - 10.1080/07328309708007331
DO - 10.1080/07328309708007331
M3 - Article
SN - 0732-8303
VL - 16
SP - 521
EP - 532
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
IS - 4-5
ER -