Synthesis and Stereochemical Assignments for 2-(α- and β-D-Arabinofuranosyl)Thiazole-4-Carboxamides
作者： Cong Jiang , Ralph H. Baur , James J. Dechter , David C. Baker
DOI: 10.1080/07328318408079424
关键词: Stereochemistry 、 Carbon-13 NMR 、 Chemistry 、 Thiazole 、 Anomer
摘要: Abstract Both 2-(α- and β-D-arabinofuranosyl) thiazole-4-carboxamides were synthesized from 2,3,5-tri-O-benzyl-1-O-(p-nitrobenzoyl)-D-arabinofuranose via the 1-cyano- 1-thioamide sugars. Anomeric assignments made based on 1H 13C NMR, as well CD spectra.
sci-hub.se 参考文章(19)
MORRIS J. ROBINS, MALCOLM MACCOSS, A “GEOMETRY-ONLY“ 1 H NMR METHOD FOR DETERMINATION OF THE ANOMERIC CONFIGURATION OF RIBOFURANOSYL COMPOUNDS Chemistry and Biology of Nucleosides and Nucleotides. pp. 311- 328 ,(1978) , 10.1016/B978-0-12-326140-3.50026-7
R. K. Robins, P. C. Srivastava, V. L. Narayanan, J. Plowman, K. D. Paull, 2-beta-D-Ribofuranosylthiazole-4-carboxamide, a novel potential antitumor agent for lung tumors and metastases. Journal of Medicinal Chemistry. ,vol. 25, pp. 107- 108 ,(1982) , 10.1021/JM00344A002
Hiroshi Ohrui, Gordon H. Jones, John G. Moffatt, Michael L. Maddox, Arild T. Christensen, Susan K. Byram, C-glycosyl nucleosides. V. Some unexpected observations on the relative stabilities of compounds containing fused five-membered rings with epimerizable substituents. Journal of the American Chemical Society. ,vol. 97, pp. 4602- 4613 ,(1975) , 10.1021/JA00849A023
Federico G. de las Heras, Piedad Fernández-Resa, Synthesis of ribosyl and arabinosyl cyanides by reaction of 1-O-acyl sugars with trimethylsilyl cyanide J. Chem. Soc., Perkin Trans. 1. ,vol. 13, pp. 903- 907 ,(1982) , 10.1039/P19820000903
Kiitiro Utimoto, Yukio Wakabayashi, Takafumi Horiie, Masaharu Inoue, Yuho Shishiyama, Michio Obayashi, Hitosi Nozaki, Cyanotrimethylsilane as a versatile reagent for introducing cyanide functionality Tetrahedron. ,vol. 39, pp. 967- 973 ,(1983) , 10.1016/S0040-4020(01)88595-1
Prem C. Srivastava, Michael V. Pickering, Lois B. Allen, David G. Streeter, Marie T. Campbell, Joseph T. Witkowski, Robert W. Sidwell, Roland K. Robins, Synthesis and antiviral activity of certain thiazole C-nucleosides. Journal of Medicinal Chemistry. ,vol. 20, pp. 256- 262 ,(1977) , 10.1021/JM00212A014
Hubert Hřebabecký, Josef Brokeš, Jiří Beránek, Preparation of the 1-(2,5-anhydro-β-d-arabinofuranosyl) derivatives of cytosine and uracil and their cleavage with hydrogen bromide Collection of Czechoslovak Chemical Communications. ,vol. 47, pp. 2961- 2968 ,(1982) , 10.1135/CCCC19822961
Mohammed A.E. Sallam, 2-phenyl-1,2,3-osotriazole C-nucleoside analogs synthesis and determination of anomeric configuration Tetrahedron Letters. ,vol. 21, pp. 183- 186 ,(1980) , 10.1016/S0040-4039(00)71408-0
Edward M. Acton, Allan N. Fujiwara, Leon Goodman, David W. Henry, Synthetic C-nucleosides: 3-(α- and β-D-arabinofuranosyl)pyrazolo[4,3-d]pyrimidine-5,7-diones Carbohydrate Research. ,vol. 33, pp. 135- 151 ,(1974) , 10.1016/S0008-6215(00)82947-X
E BESSON, J CHOPIN, Sugar ring isomerization in C-arabinosylflavones Phytochemistry. ,vol. 22, pp. 2051- 2056 ,(1983) , 10.1016/0031-9422(83)80043-0