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Volumn 7, Issue 7, 2001, Pages 1371-1382

Chemical synthesis of linear and cyclic unnatural oligosaccharides by iterative glycosidation of ketoses

Author keywords

Crown compounds; Glycosylations; Noncovalent interactions; Oligosaccharides; Thiazoles

Indexed keywords

CROWN ETHERS; OLIGOMERS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

EID: 0035312947     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010401)7:7<1371::AID-CHEM1371>3.0.CO;2-J     Document Type: Article
Times cited : (44)

References (107)
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    • The glycosylation with glycosyl phosphites has been the subject of various mechanistic studies showing that different mechanisms can operate, depending on how the substrates and the promoter are mixed, see: H. Kondo, S. Aoki, Y. Ichikawa, R. L. Halcomb, H. Ritzen, C.-H. Wong, J. Org. Chem. 1994, 59, 864-877.
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    • The small difference in chemical shifts between the two H-1 protons (Δδ = 0.2 ppm) suggested that the 1,4-dioxane ring of 24 adopts a skew-boat conformation, as favoured by the concomitant exo-anomeric effect with both the pyranoside rings. For a discussion on the exo-anomeric effect, see: S. David, The Molecular and Supramolecular Chemistry of Carbohydrates. A Chemical Introduction to the Glycosciences, Oxford University Press, Oxford, 1997, pp. 145-148.
    • (1997) The Molecular and Supramolecular Chemistry of Carbohydrates. A Chemical Introduction to the Glycosciences , pp. 145-148
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    • note
    • The distance between O1, O2, and O3 is approximately 2.8 Å, that between O8, O12, and O18 is approximately 4.4 Å, and that between O7, O13, and O17 is approximately 8.6 Å (the oxygens are numbered according to the ORTEP view of 30 in Figure 1).
  • 100
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    • note
    • The following compounds were examined: N-phthaloyl-glycine, N-acetyl-D- and L-phenylglycine, L-phenylalanine ethyl ester hydrochloride, (R)- and (S)-Mosher's acid, tetrabutylammonium iodide, (R)- and (S)-trimethyl(1-phenylethyl)ammonium iodide, (R)- and (S)-1-phenylethanol, succinimide, cesium fluoride, cesium acetate, silver nitrate.
  • 102
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    • note
    • 3 in the absence of the host.
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    • Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN
    • C. K. Johnson, ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.
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    • Johnson, C.K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.