Pd-catalyzed coupling reaction of glycosylamines with 6-chloropurines: Synthesis of 6-(β-D-mannopyranosylamino)-9H-purine and its β-D-gluco isomer, N-glycoside models for spicamycin and septacidin

Noritaka Chida, Tamotsu Suzuki, Sayaka Tanaka, Iwao Yamada

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31 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2573-2576
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number13
DOIs
Publication statusPublished - 1999 Mar 26

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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