Stereoselectivity in the electrophile-mediated cyclization of 2,3,5-tri-O-benzyl-1,2-dideoxy-d-arabino-hex-1-enitol. A stereocontrolled synthesis of 1-amino-2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-d-glucitol
1987; Elsevier BV; Volume: 171; Issue: 1 Linguagem: Inglês
10.1016/s0008-6215(00)90874-7
ISSN1873-426X
AutoresFillmore Freeman, Kirk Robarge,
Tópico(s)Polyamine Metabolism and Applications
ResumoCyclization of 2,3,5-tri-O-benzyl-1,2-dideoxy-d-arabino-hex-1-enitol (2) with mercuric acetate, mercuric trifluoroacetate, iodine, and N-bromosuccinimide gave preponderantly the allo isomer of the C-arabinofuranosyl structure. 1-Amino-2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-d-glucitol, which is a key intermediate in the synthesis of 3-(β-d-arabinofuranosyl)pyrazole[4,3-d]pyrimidine-5,7-dione (β-d-arabino epimer of oxoformycin B), was stereoselectively prepared in 48% overall yield from 2 in three steps. The stereochemical outcome of the cyclizations is also discussed.
Referência(s)