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Volumn 14, Issue 13, 2008, Pages 3987-3994

Automated solid-phase synthesis of protected oligosaccharides containing β-mannosidic linkages

Author keywords

Automation; Carbohydrates; Glycosides; Oligosaccharide synthesis; Solid phase synthesis

Indexed keywords

BIOMOLECULES; CARBOHYDRATES; CHAINS; ETHERS; OLIGOSACCHARIDES; ORGANIC COMPOUNDS; STEREOCHEMISTRY;

EID: 53849098956     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701864     Document Type: Article
Times cited : (77)

References (55)
  • 1
    • 84956473972 scopus 로고    scopus 로고
    • For recent reviews on oligosaccharide synthesis see: a Carbohydrates in Chemistry and Biology, 1 (Eds.: B. Ernst, G. W. Hart, P. Sinaÿ), Wiley-VCH, Weinheim, 2000;
    • For recent reviews on oligosaccharide synthesis see: a) Carbohydrates in Chemistry and Biology, Vol. 1 (Eds.: B. Ernst, G. W. Hart, P. Sinaÿ), Wiley-VCH, Weinheim, 2000;
  • 37
    • 0037205881 scopus 로고    scopus 로고
    • For donor-bound approach, see
    • a) For "donor-bound" approach, see: D. Crich, M. Smith, J. Am. Chem. Soc. 2002, 124, 8867;
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 8867
    • Crich, D.1    Smith, M.2
  • 38
    • 0030791784 scopus 로고    scopus 로고
    • For an intermolecular aglycon delivery (IAD) method, see: Y. Ito, T. Ogawa, J. Am. Chem. Soc. 1997, 119, 5562.
    • b) For an intermolecular aglycon delivery (IAD) method, see: Y. Ito, T. Ogawa, J. Am. Chem. Soc. 1997, 119, 5562.
  • 45
    • 53849091912 scopus 로고    scopus 로고
    • 2O posed no problem and the stock solution was stable for several days on the synthesizer.
    • 2O posed no problem and the stock solution was stable for several days on the synthesizer.
  • 46
    • 53849136786 scopus 로고    scopus 로고
    • Elongation of the saccharide can also be accomplished by acid hydrolysis of the benzylidene acelal and ensuing regioseleclive glycosylation. This option has not been investigated yet
    • Elongation of the saccharide can also be accomplished by acid hydrolysis of the benzylidene acelal and ensuing regioseleclive glycosylation. This option has not been investigated yet.
  • 50
    • 20444480974 scopus 로고    scopus 로고
    • The Crich laboratory recently employed the 2-O-propargyl ether as a minimally intrusive protecting group to overcome this erosion in selectivity: a D. Crich, P. Jayalath, Org. Lett. 2005, 7, 2277;
    • The Crich laboratory recently employed the 2-O-propargyl ether as a minimally intrusive protecting group to overcome this erosion in selectivity: a) D. Crich, P. Jayalath, Org. Lett. 2005, 7, 2277;
  • 54
    • 53849129769 scopus 로고    scopus 로고
    • 1HNMR of the 2-O-acetylated product clearly showed a downfield shift for H2.
    • 1HNMR of the 2-O-acetylated product clearly showed a downfield shift for H2.
  • 55
    • 53849092574 scopus 로고    scopus 로고
    • The use of TBAF on the ABI peptide synthesizer might have resulted in a selenoid valve failure, so we refrained from performing further Tom deprotection by automalion. This technical difficulty will be overcome by the next generation of synthesizer developed in our laboratory
    • The use of TBAF on the ABI peptide synthesizer might have resulted in a selenoid valve failure, so we refrained from performing further Tom deprotection by automalion. This technical difficulty will be overcome by the next generation of synthesizer developed in our laboratory.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.