A new stereospecific synthesis of 1,2,4-trideoxy-1,4-imino-D-erythro-pentitol

Authors
Malle, BM Lundt, I Furneaux, RH
Citation
Bm. Malle et al., A new stereospecific synthesis of 1,2,4-trideoxy-1,4-imino-D-erythro-pentitol, J CARB CHEM, 19(4-5), 2000, pp. 573-583
Citations number
20
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
ISSN journal
07328303 → ACNP
Volume
19
Issue
4-5
Year of publication
2000
Pages
573 - 583
Database
ISI
SICI code
0732-8303(2000)19:4-5<573:ANSSO1>2.0.ZU;2-Y
Abstract
1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol [(2R,3S)-3-hydroxy-2-hydroxymet hylpyrrolidine] (4) was synthesised from 2,5-di-O-tosyl-D-ribono-1,4-lacton e in 42 % overall yield. The hey steps were deoxygenation at C-2 and a ster eospecific inversion of the configuration at C-4. Compound 4 inhibited alph a-D-glucosidase (K-i = 25 mu M) and beta-D-glucosidase (K-i = 80 mu M).