Synthesis of N-protected azaoligosaccharides and their cyclic derivatives

Tetrahedron Letters

Volumn 46, Issue 14, 2005, Pages 2399-2403

  Sawada, Daisuke ^a   Takahashi, Hideyo ^a   Shiro, Moto ^b   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

Amino sugars; Azaoligosaccharide; Dimeric cycloazasugar

Indexed keywords

HETEROCYCLIC COMPOUND; NOJIRIMYCIN; OLIGOSACCHARIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 17744396680     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.057     Document Type: Article

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40. These compounds were prepared through the same steps as for the synthesis of compound 1 using 6-(4-methoxybenzyl)-2,3,4-tri-O-benzyl-D-glucono-1,5- lactone. See also Ref. 8
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42. 1H NMR is so complicated that it is difficult to know the concise structure of this compound. However, it gives a reasonable HR-Mass spectrum
43. Because the azasugar itself might be a leaving group in azaoligosaccharides, the cleavage of glycoside bond of 12 or 13 took place by TMSOTf, and same intermediate as the reaction in Table 2 was generated in situ
44. +) 461.1384, found 461.1381