Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of Tetrazolyl Derivatives of 3-Deoxy-D-glycero-D-galacto-2-onulosonic Acid (KDN) as Useful Glycosyl Donors, and Their Application for O- and C-Glycosylations
Mitsunobu NAKAMURAKazuyoshi TAKEDAHiroaki TAKAYANAGINorie ASAINaoko IBATAHaruo OGURA
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1993 Volume 41 Issue 1 Pages 26-30

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Abstract

The reaction of methyl 4, 5, 7, 8, 9-penta-O-acetyl-3-deoxy-D-glycero-D-galacto-2-nonulopyranosonate (3) with S, S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (4) gave methyl (1-phenyl-1H-tetrazol-5-yl 4, 5, 7, 8, 9-tetra-O-acetyl-3-deoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (5) and methyl (1-phenyl-5-thioxo-1H, 4H-tetrazol-4-yl4, 5, 7, 8, 9-penta-O-acetyl-2, 3-dideoxy-D-glycero-α- and -β-D-galacto-2-nonulopyranosid)onate (6, 7). The structures were elucidated by means of ultraviolet (UV), circular dichroism (CD), and 13C-nuclear magnetic resonance(13C-NMR) spectral examination, and X-ray crystal analysis. These S- and N-glycosides were applied to O-glycosylation with suitable promoters, and when palladium (II) was used as a promoter, glycosylation of 5 with 2-propanol gave the corresponding glycosides in good yield. Moreover. the S-glycoside was applied to C-glycosylations.

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