Stable d-xylose ditriflate in divergent syntheses of dihydroxy prolines, pyrrolidines, tetrahydrofuran-2-carboxylic acids, and cyclic β-amino acids

Abstract

Double nucleophilic displacement of D-xylo-ditriflate by amines, water and alkyl cyanoacetates, respectively, gave a series of bicyclic divergent intermediates for the synthesis of a wide range of highly functionalized targets,...

Stable ditriflates of D-glucose in the synthesis of iminosugars and polyhydroxyolated pipecolic acids

“…[15][16][17][18][19][20] More recently this approach has been applied to a divergent the synthesis of iminocyclopentitols and 3,4-dihydroxyprolines. 21 This paper reports the application of this methodology to a new synthesis of DAB (5) from a D-xylose ditriflates 8 and 8 (Scheme 1), together a divergent synthesis of 1-deoxymannojirimycin (DMJ, 4) and the corresponding polyhydroxylated pipecolic acid 26 from D-glucose ditriflates 18 (Scheme 2 and Scheme 3). Scheme 1.…”

“…Ditriflates 8 and 8 were obtained as previously, 21 as a 1:1 anomeric separable mixture, by treatment of D-xylose derivative mixture 7 with Tf2O and DIEA, and this mixture and its components were separately transformed into DAB (5), as shown in Scheme 1. Thus, reaction of ditriflate 8 with benzyl carbazate provided the azabicycle glycoside 9 in 83% yield, as established from the presence in its 1 H NMR of a broad singlet at 6.84 ppm and a singlet at 5.11 ppm, dues to the NH and the CH2 groups of the carbazate substituent.…”

“…This compound was identical to a sample of this compound, previously obtained. 21 On the other hand, this strategy for the synthesis of iminocyclitols from sugar ditriflates was next extended to the hexose D-glucose. This required the preparation of sugar 2,6-ditriflates 16.…”

Design, synthesis and glycosidase inhibition of DAB derivatives with C-4 peptide and dipeptide branches

“…The DAB derivatives 16 and 17 may also be viewed as peptides containing trans , trans -3,4-dihydroxy- l -proline. 26…”