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Volumn 121, Issue 4, 1999, Pages 734-753

Programmable one-pot oligosaccharide synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CARBOHYDRATE SYNTHESIS; COMPUTER PROGRAM; DATA BASE; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ASSAY; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS;

EID: 0033518559     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982232s     Document Type: Article
Times cited : (833)

References (64)
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    • note
    • A precise measurement with DMTST is difficult as its efficiency for the activation is lower than that of NIS: normally 4 equiv of DMTST is used for the glycosylation and the reaction is much slower than that of NIS. We observed that 2 equiv could be enough to complete a reaction with 1 equiv of thioglycoside within a certain time. For the competition reactions, the conditions were exactly the same as those with NIS-TfOH (see general procedure in Experimental Section), except that DMTST was taken as 2 mole equiv relative to the donors (each I mole equiv) and the reaction was continued for 3 h. This measurement can only be performed between donors with small reactivity differences.
  • 47
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    • note
    • The elevated reactivity of N-Troc-protected glucosamines might be the result of the electron-donating property of the N-trichloroethoxycarbonyl group to stabilize the intermediate as shown in the following tentative mechanism. Research is underway to test the proposal.
  • 54
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    • note
    • For example, in the synthesis of the lactoside 9 (see scheme below), in addition to the target disaccharide 9 (65%), the succinimide product 58 (15%) was also isolated as a byproduct.
  • 55
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    • note
    • 48 (1776) 9 (6.9) 58 2.0 equiv 65% 15% The low reactivity of the 4-OH of glucoside 10 (RRV = 8.4), coupled with an increased reactivity of the transient intermediate cation derived from the initial reaction of galactoside 48 (RRV = 1776) with iodonium ion, could explain the formation of 57.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.