Enantiomerically Pure 7-Oxabicyclo[2.2.1]Hept-5-En-2-Yl Derivatives (Naked Sugars) as Synthetic Intermediates .22. Stereoselective Synthesis of (1r)-1-C-(6-Amino-7h-Purin-8-Yl)-1,4-Anhydro-2,3-Dideoxy-3-Fluoro-D-Eryt Hro-Pentitol

The "naked sugar" (+)-(1R,2S,4R)-2-cyano-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl (1S)-camphanate [(+)-3] (Diels-Alder adduct of furan with 1-cyanovinyl (1S)-camphanate) was converted into (1R)-1-C-(6-amino-7H-purin-8-yl)-1,4-anhydro-2,3-dideoxy-3-fluoro-D-eryt hro-pentitol [(+)-2] in nine synthetic steps and 12% overall yield.


Published in:
Synlett, 8, 676-678
Year:
1992
ISSN:
0936-5214
Keywords:
Note:
Univ lausanne,chem sect,2 rue barre,ch-1005 lausanne,switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-12-03


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