Factors affecting stereocontrol during glycosidation of 2,3-oxazolidinone-protected 1-tolylthio-N-acetyl-D-glucosamine

Journal of Organic Chemistry

Volumn 70, Issue 10, 2005, Pages 4195-4198

  Wei, Peng ^a   Kerns, Robert J ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; ALCOHOLS; CHEMICAL REACTIONS; FREE RADICALS; SUGARS;

DONOR ACTIVATION; GLYCOSIDATION; STEREOCHEMICAL CONTROL;

AMINES;

1 TOLYLTHIO N ACETYLGLUCOSAMINE; 2,3 OXAZOLIDINONE; GLUCOSAMINE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DERIVATIZATION; GLYCOSIDATION; REACTION ANALYSIS; RESIDUE ANALYSIS; STEREOCHEMISTRY; STRAIN DIFFERENCE; STRUCTURE ANALYSIS;

GLUCOSAMINE; GLYCOCONJUGATES; GLYCOSIDES; GLYCOSYLATION; OXAZOLIDINONES; STEREOISOMERISM;

EID: 18744406719     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047812o     Document Type: Article

References (18)

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8. PST is a costly and difficult reagent to employ. It must be prepared in situ from benzenesulfenyl chloride and silver triflate, both of which are unstable and/or costly. See: (a) Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1998, 61, 1702-1706.
9. 2O either have been insufficient at promoting glycosylation of N-unsubstituted 2,3-oxazolidinone protected donors or form detrimental adducts with the oxazolidinone nitrogen, sequestering activating agent, and/or resulting in degradation of donor.
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