A new stereoselective approach to a selectively protected derivative of D-pinitol and its evaluation as a-L-rhamnopyranose mimetic

Catelani, Giorgio and D'Andrea, Felicia and Griselli, Alessio and Toma, Lucio and Guazzelli, Lorenzo and Legnani, Laura (2008) A new stereoselective approach to a selectively protected derivative of D-pinitol and its evaluation as a-L-rhamnopyranose mimetic. Tetrahedron Letters, 49 (29-30). pp. 4534-4536. ISSN 0040-4039

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Abstract

SUMMARY The synthesis of 3,5-di-O-benzyl-D-pinitol has been stereoselectively accomplished through intramolecular aldolization of 2,6-di-O-benzyl-4-O-methyl-L-lyxo-hexos-5-ulose followed by reduction with NaBH( OAc)3. Computational analysis [DFT calculations at the B3LYP/6-31G(d) level] suggests that D-pinitol in water largely prefers the conformation corresponding to the 1C4 one of a a-L-rhamnopyranoside unit, being thus a good candidate for its mimicking.

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