TY - JOUR
T1 - Oxidation products of C-4 and C-7 hydroxyls in the methyl α-glycoside derivatives of KDN
AU - Kai, Toshitsugu
AU - Sun, Xue
AU - Takayanagi, Hiroaki
AU - Furuhata, Kimio
PY - 1997/1/1
Y1 - 1997/1/1
N2 - A regioselective protection of hydroxyl groups in the methyl ester-methyl α-glycoside derivative of KDN was demonstrated. Isopropylidenation of methyl (methyl 3-deoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate (1) gave mono-(8, 9) and di-(5, 7: 8, 9) O-isopropylidene derivatives. Benzoylation of methyl (methyl 3-deoxy-8, 9-O-isopropylidene-α-D-glycero-D-galacto-2-nonulopyranosid)onate (7) gave di-(4, 5) and tri-(4, 5, 7) O-benzoates. Through these reactions, it was found that the reactivity of the hydroxyl groups was different from that of methyl β-glycoside of KDN. Oxidation products of C-4 and C-7 hydroxyl groups (6 and 11) were synthesized from these compounds.
AB - A regioselective protection of hydroxyl groups in the methyl ester-methyl α-glycoside derivative of KDN was demonstrated. Isopropylidenation of methyl (methyl 3-deoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate (1) gave mono-(8, 9) and di-(5, 7: 8, 9) O-isopropylidene derivatives. Benzoylation of methyl (methyl 3-deoxy-8, 9-O-isopropylidene-α-D-glycero-D-galacto-2-nonulopyranosid)onate (7) gave di-(4, 5) and tri-(4, 5, 7) O-benzoates. Through these reactions, it was found that the reactivity of the hydroxyl groups was different from that of methyl β-glycoside of KDN. Oxidation products of C-4 and C-7 hydroxyl groups (6 and 11) were synthesized from these compounds.
UR - https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0009405595&origin=inward
UR - https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=0009405595&origin=inward
U2 - 10.1080/07328309708007332
DO - 10.1080/07328309708007332
M3 - Article
SN - 0732-8303
VL - 16
SP - 533
EP - 540
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
IS - 4-5
ER -