- Synthesis and investigation of polyhydroxylated pyrrolidine derivatives as novel chemotypes showing dual activity as glucosidase and aldose reductase inhibitors
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Diabetes is a multi-factorial disorder that should be treated with multi-effective compounds. Here we describe the access to polyhydroxylated pyrrolidines, belonging to the D-gluco and D-galacto series, through aminocyclization reactions of two differenti
- Guazzelli, Lorenzo,D'Andrea, Felicia,Sartini, Stefania,Giorgelli, Francesco,Confini, Gianluca,Quattrini, Luca,Piano, Ilaria,Nencetti, Susanna,Orlandini, Elisabetta,Gargini, Claudia,La Motta, Concettina
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supporting information
(2019/09/30)
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- Open-chain acetonides of D-galactono-l,4-lactone as starting materials for pyrrolidines, azepanes and 5-azidomethyltetrahydrofuran-2-carboxylates: Monomers for polyhydroxylated nylon and for tetrahydrofuran carbopeptoids
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Treatment of D-gaIactono-l,4-lactone with dimethoxypropane in acetone in the presence of tosic acid forms methyl 2,3:5,6-di-0-isopropylidene-D-galactonate 6 (with only the secondary hydroxy group at C-4 unprotected) and methyl 2,3:4,5-di-O-isopropyIidene-D-galactonate 5 (with only the primary hydroxy group at C-6 unprotected) in yields of 20% and 78%, respectively. The value of such easily accessible intermediates is illustrated by the synthesis of l,4-dideoxy-l,4-imino-D-glucitol 16 (a pyrrolidine), and for the efficient preparation of 6-azido-6-deoxy-D-galactono1,4-lactone 22. The conversion of 22 to a seven-rhembered galactonolactam 21 (a tetrahydroxycaprolactam) may provide access to hydroxylated nylon polymers. The galactonolactam 21 has no significant inhibitory effect on a number of glycosidases. Reaction of 22 with triflic anhydride gives two epimeric 5-(azidomethyl)tetrahydrofuran-2carboxylates which provide starting materials for two series of carbopeptoids, one of which probably has a helical structure and the other a structure reminiscent of a β-turn.
- Long, Daniel D.,Stetz, Rebecca J. E.,Nash, Robert J.,Marquess, Daniel G.,Lloyd, Janet D.,Winters, Ana L.,Asano, Naoki,Fleet, George W. J.
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p. 901 - 908
(2007/10/03)
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- A SHORT, VERSATILE APPROACH TO POLYHYDROXYLATED PYRROLIDINES UTILIZING A REDUCTIVE ELIMINATION-REDUCTIVE AMINATION AS A KEY STEP
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An efficient synthesis of epimeric alpha-vinyl pyrrolidines starting from methyl 4,6-O-benzyliden gluco- and galactopyranosides gave ready access to hydroxylated pyrrolidines.
- Bernotas, Ronald C.
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p. 469 - 472
(2007/10/02)
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- POLYHYDROXYLATED PYRROLIDINES FROM SUGAR LACTONES: SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-D-GLUCITOL FROM D-GALACTONOLACTONE AND SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-ALLITOL, 1,4-DIDEOXY-1,4-IMINO-D-RIBITOL, AND (2S,3R,4S)-3,4-DIHYDROXYPROLINE FROM D-GULONOLACTONE
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The use of readily available sugar lactones in the synthesis of polyhydroxylated pyrrolidines is illustrated by the preparation of the glucosidase inhibitor 1,4-dideoxy-1,4-imino-D-glucitol from D-galactonolactone and by the conversion of D-gulonolactone into 1,4-dideoxy-1,4-imino-D-allitol, 1,4-dideoxy-1,4-imino-D-ribitol, and (2S,3R,4S)-3,4-dihydroxyproline.
- Fleet, George W. J.,Son, Jong Chan
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p. 2637 - 2648
(2007/10/02)
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- SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-D-GLUCITOL, A GLUCOSIDASE INHIBITOR
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1,2:5,6-Di-O-isopropylidene-D-glucitol was converted via its 1,4-dimethanesulfonate into the 1-azido-4-methanesulfonate which, after deprotection and treatment with barium hydroxide, afforded a 9:1 mixture of the corresponding 3,4- and 4,5-anhydro derivat
- Kuszmann, Janos,Kiss, Laszlo
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