TY - JOUR
T1 - Pd-catalyzed coupling reaction of glycosylamines with 6-chloropurines
T2 - Synthesis of 6-(β-D-mannopyranosylamino)-9H-purine and its β-D-gluco isomer, N-glycoside models for spicamycin and septacidin
AU - Chida, Noritaka
AU - Suzuki, Tamotsu
AU - Tanaka, Sayaka
AU - Yamada, Iwao
PY - 1999/3/26
Y1 - 1999/3/26
N2 - The first example of preparation of 6-(β-D-mannopyranosylamino)-9H- purine (8), whose N-glycosidic linkage corresponds to a natural antibiotic, spicamycin, by Pd-catalyzed coupling reaction of a mannopyranosylamine with 9-protected-6-chloropurine, followed by deprotection, is described. Its β- D-gluco isomer (11) was also synthesized. This work established the procedure to construct the novel N-glycoside, in which the pyranose unit is connected to the amino group at C(6) of adenine moiety.
AB - The first example of preparation of 6-(β-D-mannopyranosylamino)-9H- purine (8), whose N-glycosidic linkage corresponds to a natural antibiotic, spicamycin, by Pd-catalyzed coupling reaction of a mannopyranosylamine with 9-protected-6-chloropurine, followed by deprotection, is described. Its β- D-gluco isomer (11) was also synthesized. This work established the procedure to construct the novel N-glycoside, in which the pyranose unit is connected to the amino group at C(6) of adenine moiety.
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U2 - 10.1016/S0040-4039(99)00250-6
DO - 10.1016/S0040-4039(99)00250-6
M3 - Article
AN - SCOPUS:0033605936
SN - 0040-4039
VL - 40
SP - 2573
EP - 2576
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 13
ER -