TY - JOUR
T1 - Synthesis and structure of 2-pyransoylperimidines
AU - Smellie, Iain A. S.
AU - Fromm, Andreas
AU - Moggach, Stephen A.
AU - Paton, R. Michael
PY - 2011/1/3
Y1 - 2011/1/3
N2 - The first examples of 2-pyranosylperimidines are reported. The beta-D-glucopyranosyl nitrile oxide 5, generated by base-induced dehydrochlorination of the hydroximoyl chloride 4, reacted with 1,8-diaminonaphthalene to afford the 2-(beta-D-glucopyranosyl)perimidine 8. The D-xylo-, D-galacto-, D-manno- and D-glycero analogues 12, 15, 16 and 19 were prepared similarly. The glycals 9 and 13 were formed as by-products resulting from elimination of acetic acid from the corresponding pyranosylperimidines. The structure of D-glucose-derived perimidine 8 was established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.
AB - The first examples of 2-pyranosylperimidines are reported. The beta-D-glucopyranosyl nitrile oxide 5, generated by base-induced dehydrochlorination of the hydroximoyl chloride 4, reacted with 1,8-diaminonaphthalene to afford the 2-(beta-D-glucopyranosyl)perimidine 8. The D-xylo-, D-galacto-, D-manno- and D-glycero analogues 12, 15, 16 and 19 were prepared similarly. The glycals 9 and 13 were formed as by-products resulting from elimination of acetic acid from the corresponding pyranosylperimidines. The structure of D-glucose-derived perimidine 8 was established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.
UR - http://www.scopus.com/inward/record.url?scp=78650198911&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2010.09.028
DO - 10.1016/j.carres.2010.09.028
M3 - Article
SN - 0008-6215
VL - 346
SP - 43
EP - 49
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 1
ER -