Novel carbohydrate scaffolds. Assembly of a uridine-mannose scaffold based on tunicamycin

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 855-858

  Silva, Domingos J ^a,b   Sofia, Michael J ^a  

^a Department of Biological Research   (United States)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Antibiotics; Carbohydrates; Combinatorial chemistry

Indexed keywords

DISACCHARIDE; MANNOSE; TUNICAMYCIN; URIDINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; GLYCOSYLATION; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034606909     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02209-1     Document Type: Article

References (22)

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22. H-C=159 Hz, characteristic of β-mannosides: Bock, K.; Pedersen, C. J. Chem. Soc., Perkin Trans. 2 1974, 293-297. The β:α selectivity of this glycosylation (1.8:1) is lower than the selectivities generally obtained with Crich's procedure (Ref. 10) and may be associated with particular stereoelectronic characteristics of the uridyl acceptor, since the mannosyl donor has been shown to afford high β/α selectivities with primary glycosyl acceptors (Ref. 10b).