X-Ray Structure of the Key Synthetic Intermediate of a Cancer-Related Sialyl-Tn Antigen Analogue.

Autor: Renaudet, Olivier, Philouze, Christian, Bailly, Corinne, Durif, André, Dumy, Pascal
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Zdroj: Journal of Chemical Crystallography; Feb2011, Vol. 41 Issue 2, p204-208, 5p, 3 Diagrams, 2 Charts
Abstrakt: We report herein the synthesis and the X-ray crystal structure of 2-azido-2-deoxy-3,4- O-isopropylidene-α- d-galactopyranosyl- N-oxyphthalimide 3 which is the key-precursor of a cancer-related STn antigen analogue 5. Compound 3 crystallizes from a mixture of dichloromethane/pentane as colorless orthorhombic needles in P2 2 2 space group with the following cell parameters: a = 14.039(2) Å; b = 16.574(3) Å; c = 8.038(1) Å. The hexapyranose ring of 3 adopts a twisted boat according to the Cremer and Pople puckering parameters (Cremer and Pople, J Am Chem Soc 97:1354, 1975) whereas the structure determination of the corresponding deprotected intermediate 4 (orthorombic colorless prisms, P2 2 2 space group, a = 4.927(3) Å; b = 13.423(2) Å; c = 22.744(3) Å) has revealed a quasi perfect chair. Index Abstract: We report herein the synthesis and the X-ray crystal structure of 2-azido-2-deoxy-3,4- O-isopropylidene-α- d-galactopyranosyl- N-oxyphthalimide 3 which is the key-precursor of a cancer-related STn antigen analogue 5.[Figure not available: see fulltext.] [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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