Synthetic Approach Toward Antibiotic Tunicamycins, 4. X-Ray Crystal Structure Analysis of a Higher-Carbon Nitro Sugar |
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| Authors: | Tetsuo Suami Yoshimasa Fukuda Junji Yamamoto Yoshihiko Saito Masatoki Ito Shigeru Ohba |
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| Institution: | Department of Applied Chemistry , Faculty of Science and Technology Keio University , Hiyoshi, Yokohama, 223, Japan |
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| Abstract: | Abstract 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-O-isopropylidene-5-nitro-β-D-ribofuranoside to methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-α-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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| Keywords: | Phase‐transfer glycosylation Scented alcohols Flavorant‐release additives |
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