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 α-l-rhamnopyranoside unit, being thus a good candidate for its mimicking.

Catelani, G., D'Andrea, F., Griselli, A., Guazzelli, L., Legnani, L., Toma, L. (2008). A new stereoselective approach to a selectively protected derivative of D-pinitol and its evaluation as alpha-L-rhamnopyranose mimetic. TETRAHEDRON LETTERS, 49(29-30), 4534-4536 [10.1016/j.tetlet.2008.05.040].

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

LEGNANI, LAURA;
2008

Abstract

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 α-l-rhamnopyranoside unit, being thus a good candidate for its mimicking.
Articolo in rivista - Articolo scientifico
α-l-Rhamnopyranose mimetic; Computational analysis; d-Pinitol; Intramolecular aldol condensation;
English
4534
4536
3
Catelani, G., D'Andrea, F., Griselli, A., Guazzelli, L., Legnani, L., Toma, L. (2008). A new stereoselective approach to a selectively protected derivative of D-pinitol and its evaluation as alpha-L-rhamnopyranose mimetic. TETRAHEDRON LETTERS, 49(29-30), 4534-4536 [10.1016/j.tetlet.2008.05.040].
Catelani, G; D'Andrea, F; Griselli, A; Guazzelli, L; Legnani, L; Toma, L
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/351998
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