TY - JOUR
T1 - Synthetic approach toward antibiotic tunicamycins, 4.+ x-ray crystal structure analysis of a higher-carbon nitro sugar
AU - Suami, Tetsuo
AU - Fukuda, Yoshimasa
AU - Yamamoto, Junji
AU - Saito, Yoshihiko
AU - Ito, Masatoki
AU - Ohba, Shigeru
PY - 1982/1/1
Y1 - 1982/1/1
N2 - A higher-carbon carbohydrate, a derivative of undecose has been synthesized by the potassium fluoride-catalyzed addition of a nitro sugar to a sugar aldehyde. The addition of methyl 5-de-oxy-2,3-0-isopropylidene-5-nitro-6-D-ribofuranoside to methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-0-isopropylidene-a-D-galacto-dialdopyranoside-(1,5) yielded a single diastereomer of the nitro undecose derivative. The absolute configuration of two chiral centers of the derivative has been established by the X-ray crystal structure analysis.
AB - A higher-carbon carbohydrate, a derivative of undecose has been synthesized by the potassium fluoride-catalyzed addition of a nitro sugar to a sugar aldehyde. The addition of methyl 5-de-oxy-2,3-0-isopropylidene-5-nitro-6-D-ribofuranoside to methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-0-isopropylidene-a-D-galacto-dialdopyranoside-(1,5) yielded a single diastereomer of the nitro undecose derivative. The absolute configuration of two chiral centers of the derivative has been established by the X-ray crystal structure analysis.
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U2 - 10.1080/07328308208085075
DO - 10.1080/07328308208085075
M3 - Article
AN - SCOPUS:0020284410
SN - 0732-8303
VL - 1
SP - 9
EP - 19
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
IS - 1
ER -