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Synthesis 2011(20): 3318-3322  
DOI: 10.1055/s-0030-1260225
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New Highly Efficient Stereoselective Synthesis of d-threo-PDMP

Giuliana Righi*a, Paolo Bovicellib, Francesca Montinic, Federica Melonic, Emanuela Mandicc, Romina Pelagallic
a C.N.R. Institute of Biomolecular Chemistry (ICB), Unity of Rome, c/o Department of Chemistry, Sapienza University, P. le A. Moro 5, Box No. 34 Roma-62, 00185 Roma, Italy
Fax: +39(064)9913628; e-Mail: giuliana.righi@cnr.it;
b C.N.R. ICB, Unity of Sassari, Traversa La Crucca 3 - Baldanica, 07040 Sassari, Italy
c Department of Chemistry, Sapienza University, P. le A. Moro 5, 00185 Roma, Italy
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Publication History

Received 16 May 2011
Publication Date:
27 September 2011 (online)

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Abstract

Starting from a suitably functionalized aziridine, a highly efficient stereoselective synthesis of (1R,2R)-phenyl-2-decanoyl­amino-3-morpholinopropan-1-ol (d-threo-PDMP) is described. The approach, based on the ring expansion of the aziridine ring to oxazoline, could be applicable to the synthesis of many analogues with different amide chains and sugar mimic portions.

Key words

regioselectivity - ring opening - glycosidases - inhibitors - ring expansion

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This task was accomplished in 7 steps with 4 chromato-graphic separations.