SYNTHESIS OF THE (ALPHA,ALPHA-DIFLUOROALKYL)PHOSPHONATE ANALOG OF PHOSPHOSERINE

Authors
BERKOWITZ DB SHEN QR MAENG JH
Citation
Db. Berkowitz et al., SYNTHESIS OF THE (ALPHA,ALPHA-DIFLUOROALKYL)PHOSPHONATE ANALOG OF PHOSPHOSERINE, Tetrahedron letters, 35(35), 1994, pp. 6445-6448
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
35
Year of publication
1994
Pages
6445 - 6448
Database
ISI
SICI code
0040-4039(1994)35:35<6445:SOT(AO>2.0.ZU;2-Y
Abstract
The synthesis of the (alpha,alpha-difluoroalkyl)phosphonate analogue o f L-phosphoserine, 5, in a form appropriate for solid phase peptide sy nthesis, is reported. Two independent routes are described, starting f rom L-serine or (R)-isopropylideneglycerol. In each case, PCF2-C bond formation is achieved by triflate displacement with diethyl lithiodifl uoromethylphosphonate.