Synthesis and biological evaluation of (2-hydroxyethyl) 2-deoxy-alpha-D-threo-pyranoside 3,4,2 '-trisphosphate, a mimic of the second messenger inositol 1,4,5-trisphosphate

Authors
Roussel, F Hilly, M Chretien, F Mauger, JP Chapleur, Y
Citation
F. Roussel et al., Synthesis and biological evaluation of (2-hydroxyethyl) 2-deoxy-alpha-D-threo-pyranoside 3,4,2 '-trisphosphate, a mimic of the second messenger inositol 1,4,5-trisphosphate, J CARB CHEM, 18(6), 1999, pp. 697-707
Citations number
16
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
ISSN journal
07328303 → ACNP
Volume
18
Issue
6
Year of publication
1999
Pages
697 - 707
Database
ISI
SICI code
0732-8303(1999)18:6<697:SABEO(>2.0.ZU;2-B
Abstract
(2-Hydroxyethyl) 2-deoxy-alpha-D-threo-pentopyranoside 3,4,2'-trisphosphate (3) has been prepared starting from allyl-alpha-D-xylopyranoside. The suit ably protected 2-deoxy intermediate obtained by judicious selective protect ion and deprotection has been phosphorylated using the phosphoramidite meth odology. Final deprotection gave the expected analogue of myo-inositol 1,4, 5-trisphosphate.