Diastereoselective synthesis of L-(+)-homolamivudine

Authors
Khan, N Bastola, SR Witter, KG Scheiner, P
Citation
N. Khan et al., Diastereoselective synthesis of L-(+)-homolamivudine, TETRAHEDR L, 40(51), 1999, pp. 8989-8992
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
51
Year of publication
1999
Pages
8989 - 8992
Database
ISI
SICI code
0040-4039(199912)40:51<8989:DSOL>2.0.ZU;2-L
Abstract
L-homolamivudine (2a, (2R,5R)-(+)-cis-5-(1-cytosinylmethy])-2-hydroxymethyl -1,3-oxathiolane) and its 5-fluoro congener (2b, L-homoFTC) have been prepa red from (R)-glycidol by diastereoselective synthesis. Enantioselectivity r esulted from stereoselective cyclothioacetalization that preferentially gav e the (2R,5R)-cis-2,5-disubstituted-1,3-oxathiolane (5), cis/trans = 5.7. ( C) 1999 Elsevier Science Ltd. All rights reserved.