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Synthesis 1992; 1992(11): 1133-1136
DOI: 10.1055/s-1992-26321
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Convenient Iodonium-Promoted Stereoselective Synthesis of 2-Deoxy-α-glycosides by Use of S-(2-Deoxyglycosyl) Phosphorodithioates as Donors

Lothar Laupichler* , Henry Sajus, Joachim Thiem
  • *Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King Platz 6, D-2000 Hamburg 13, Germany
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Publication History

Publication Date:
17 September 2002 (online)

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S-(2-Deoxyglycosyl) O,O-diethyl phosphorodithioates, easily accessible from glycals, are convenient precursors for glycosylation in the presence of promoters such as N-iodosuccinimide or iodonium bis (2,4,6-trimethylpyridine) perchlorate. In a series of transformations both the α- and β-glycosyl donors were attached stereoselectively to acceptor sugar molecules [1,2: 3,4-di-O-isopropylidene-α-D-galactopyranose (1), benzyl 3-O-benzyl-2,6-dideoxy-β-L-ribo-hexopyranoside (2) or benzyl 4-O-benzyl-2,6-dideoxy-β-L-ribo-hexopyranoside (3)] in primary and secondary positions in short reaction times and generally convincing yields.