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 alfa-L-rhamnopyranoside unit, being thus a good candidate for its mimicking.
A new stereoselective approach to a selectively protected derivative of D-pinitol and its evaluation as alfa-L-rhamnopyranose mimetic
CATELANI, GIORGIO;D'ANDREA, FELICIA;GUAZZELLI, LORENZO;
2008-01-01
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 alfa-L-rhamnopyranoside unit, being thus a good candidate for its mimicking.File in questo prodotto:
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