TY - JOUR
T1 - Syntheses of 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonic acid (KDN2en) and its hydrogenation products
AU - Sun, Xue
AU - Kai, Toshitsugu
AU - Takayanagi, Hiroaki
AU - Furuhata, Kimio
PY - 1997/1/1
Y1 - 1997/1/1
N2 - Methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate (5) was synthesized from KDN methyl ester 2 with a catalytic amount of concentrated sulfuric acid in acetic anhydride, or from 2-chloro-KDN methyl ester 4 with DBU in good yield. Hydrogenation of 4 and 5 with 10% Pd-C gave 2-deoxy-2-Hax-KDN 8 and 2-deoxy-2-Heq-KDN derivative 11 in high yield, respectively. The structures of these compounds were elucidated from the MS, elemental analysis, 1H NMR and 13C NMR data.
AB - Methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate (5) was synthesized from KDN methyl ester 2 with a catalytic amount of concentrated sulfuric acid in acetic anhydride, or from 2-chloro-KDN methyl ester 4 with DBU in good yield. Hydrogenation of 4 and 5 with 10% Pd-C gave 2-deoxy-2-Hax-KDN 8 and 2-deoxy-2-Heq-KDN derivative 11 in high yield, respectively. The structures of these compounds were elucidated from the MS, elemental analysis, 1H NMR and 13C NMR data.
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U2 - 10.1080/07328309708007333
DO - 10.1080/07328309708007333
M3 - Article
SN - 0732-8303
VL - 16
SP - 541
EP - 547
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
IS - 4-5
ER -