SYNTHESIS OF NOVEL D-2',3'-DIDEOXY-2',3'-ENDO-METHYLENE NUCLEOSIDES

Authors
HONG JH CHUN BK CHU CK
Citation
Jh. Hong et al., SYNTHESIS OF NOVEL D-2',3'-DIDEOXY-2',3'-ENDO-METHYLENE NUCLEOSIDES, Tetrahedron letters, 39(3-4), 1998, pp. 225-228
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
3-4
Year of publication
1998
Pages
225 - 228
Database
ISI
SICI code
0040-4039(1998)39:3-4<225:SONDN>2.0.ZU;2-6
Abstract
Asymmetric synthesis of D2',3'-dideoxy-2',3'-endo-methylene nucleoside s was achieved via the intermediate 2,3-endo-methylene pentofuranoyl c hloride 6, which was prepared from 1,2:5,6-Di-O-isopropylidene-D-manni tol 1 with high stereoselectivity (only a chlorosugar). The SN2 type c ondensation of 6 with sodium salt of adenine and silyated N-4-benzoylc ytosine gave the desired beta-nucleosides as major isomers (beta:alpha = 2.5:1 and 2:1, respectively). (C) 1997 Elsevier Science Ltd. All ri ghts reserved.