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Synthesis 2010(10): 1666-1672  
DOI: 10.1055/s-0029-1218719
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Mannose Hexasaccharide Related to the Cell Wall Mannan of Candida dubliniensis and Trychophyton mentagrophytes

Guanghui Zong, Naili Yu, Yanjun Xu, Jianjun Zhang*, Daoquan Wang, Xiaomei Liang*
Key Laboratory of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China
Fax: +86(10)62732219; e-Mail: zhangjianjun@cau.edu.cn; e-Mail: nmrlab@cau.edu.cn;
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Publication History

Received 14 January 2010
Publication Date:
26 March 2010 (online)

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Abstract

2,6-Branched mannose hexasaccharide 1 related to the cell wall polysaccharide of Candida dubliniensis and Trychophyton mentagrophytes was concisely synthesized from 4-methoxyphenyl α-d-mannopyranoside (6) in 11 steps in 26% total yield. The efficiency of the synthesis relies on the preparation of a trisaccharide acceptor 2 with three free hydroxy groups, which could be glycosylated with trichloroacetimidate 19 to provide the protected hexasaccharide 20 in one step. Compound 2 was obtained via sequential assembly from the building blocks, 2,6-di-O-allyloxycarbonyl-3,4-di-O-benzoyl-α-d-mannopyranose trichloroacetimidate (3), 4-methoxyphenyl 3,4-di-O-benzoyl-α-d-mannopyranoside (4), and 4-methoxyphenyl 4-O-acetyl-3-O-benzoyl-α-d-mannopyranoside (5). Structures of target compound and intermediates were characterized by ¹H and ¹³C NMR, MS, HRMS, and elemental analysis.

Key words

synthesis - oligosaccharide - mannose - Candida dubliniensis - Trychophyton mentagrophytes

    References

  • 1a Kawarasaki I. Takeda T. Ogihara Y. Shimonaka H. Nozawa Y. Chem. Pharm. Bull.  1979,  27:  2073 
    Google Scholar
  • 1b Takeda T. Kawarasaki I. Ogihara Y. Carbohydr. Res.  1981,  89:  301 
    Google Scholar
  • 1c Liqibárová I. Matulová M. Machová E. Capek P. Carbohydr. Polym.  2007,  68:  191 
    Google Scholar
  • 2 Hay RJ. J. Dermatol.  1982,  106:  1 
    Google Scholar
  • 3a Sullivan DJ. Westerneng TJ. Haynes KA. Bennet DE. Coleman DC. Microbiology  1995,  141:  1507 
    Google Scholar
  • 3b Brown DM. Jabra-Rizk MA. Falkler WA. Baqui AAMA. Meiller TF. Pediatr. Dent.  2000,  22:  234 
    Google Scholar
  • 4 Roberts IS. Annu. Rev. Microbiol.  1996,  50:  285 
    CrossrefGoogle Scholar
  • 5a Jones C. An. Acad. Bras. Cienc.  2005,  77:  293 
    Google Scholar
  • 5b Takamatsu-Matsushita N. Yamaguchi N. Kawasaki M. Yamashita Y. Koga T. Oral Microbiol. Immunol.  1996,  11:  220 
    Google Scholar
  • 5c Zuurmond HM. Veeneman GH. Marel GA. Boom JH. Carbohydr. Res.  1993,  241:  153 
    Google Scholar
  • 5d Heidelberg T. Martin OR. J. Org. Chem.  2004,  69:  2290 
    Google Scholar
  • 5e Fekete A. Gyergyoi K. Kover KE. Bajza I. Liptak A. Carbohydr. Res.  2006,  341:  1312 
    Google Scholar
  • 6a Nin J. Kong F. Tetrahedron Lett.  1999,  40:  1357 
    Google Scholar
  • 6b Nin J. Heng L. Kong F. Carbohydr. Res.  2002,  337:  1159 
    Google Scholar
  • 6c Nin J. Heng L. Kong F. Tetrahedron Lett.  2002,  43:  673 
    Google Scholar
  • 6d Xing Y. Nin J. Tetrahedron: Asymmetry  2003,  14:  1275 
    Google Scholar
  • 7a Yan S. Wu X. Liang X. Zhang J. Chin. Chem. Lett.  2009,  20:  582 
    Google Scholar
  • 7b Zong G. Yan S. Liang X. Zhang J. Wang D. Chin. Chem. Lett.  2009,  20:  127 
    Google Scholar
  • 7c Yan S. Liang X. Diao P. Yang Y. Zhang J. Wang D. Carbohydr. Res.  2008,  343:  3107 
    Google Scholar
  • 8 Faure R. Shiao TC. Damerval S. Roy R. Tetrahedron Lett.  2007,  48:  2385 
    CrossrefGoogle Scholar
  • 9 Copeland C. Stick RV. Aust. J. Chem.  1978,  31:  1371 
    CrossrefGoogle Scholar
  • 10 Schmidt RR. Kinzy W. Adv. Carbohydr. Chem. Biochem.  1994,  50:  21 
    PubMedGoogle Scholar