I. Izquierdo, M. T. Plaza, Miguel A. Rodríguez
Mar 13, 2006
Citations
0
Influential Citations
13
Citations
Journal
Tetrahedron
Abstract
Abstract The readily available 3-O-benzoyl-4-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-β- d -fructopyranose ( 5 ) was straightforwardly transformed into its d -psico epimer ( 8 ), after O-debenzoylation followed by oxidation and reduction, which caused the inversion of the configuration at C(3). Compound 8 was treated with lithium azide yielding 5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-α- l -tagatopyranose ( 9 ) that was transformed into the related 3,4-di-O-benzyl derivative 10 . Cleavage of the acetonide in 10 to give 11 , followed by regioselective 1-O-pivaloylation to 12 and subsequent catalytic hydrogenation gave (2R,3S,4R,5S)-3,4-dibenzyloxy-2,5-bis(hydroxymethyl)-2′-O-pivaloylpyrrolidine ( 13 ). Stereochemistry of 13 could be determined after O-deacylation to the symmetric pyrrolidine 14 . Total deprotection of 14 gave 2,5-imino-2,5-dideoxy- d -galactitol ( 15 , DGADP).