Synthetic Approach Toward Antibiotic Tunicamycins, 4. X-Ray Crystal Structure Analysis of a Higher-Carbon Nitro Sugar
- 1 January 1982
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 1 (1) , 9-19
- https://doi.org/10.1080/07328308208085075
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.This publication has 8 references indexed in Scilit:
- Synthetic Approach toward Antibiotic TunicamycinsBulletin of the Chemical Society of Japan, 1981
- Isolation and structures of components of tunicamycin.Agricultural and Biological Chemistry, 1980
- Nitroalkane synthesis. A convenient method for aldehyde reductive nitromethylationTetrahedron Letters, 1978
- A rationalization on the relative thermodynamic stabilities of fused five-membered tetrahydrofurans with epimerizable substituents. An anomeric effect in furanosesThe Journal of Organic Chemistry, 1977
- Derivatives of phosphonate and vinyl phosphate analogs of D-ribose 5-phosphateCarbohydrate Research, 1974
- TUNICAMYCIN, A NEW ANTIBIOTIC. IThe Journal of Antibiotics, 1971
- Sulfoxide-Carbodiimide Reactions. I. A Facile Oxidation of AlcoholsJournal of the American Chemical Society, 1965
- Raney Nickel and Platinized Rany Nickel with Higher Catalytic ActivitiesBulletin of the Chemical Society of Japan, 1959