(3R,4S,5R,6R,7S)-3,4,5,7-Tetrahydroxyconidine, an azetidine analogue of 6,7-diepicastanospermine and a conformationally constrained d-deoxyaltronojirimycin, from l-arabinose

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

“…The first reported example consisted of an efficient synthesis of azetidines. [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).…”

Conformationally constrained fused bicyclic iminosugars: synthetic challenges and opportunities

“…89 The same group also synthesized tetrahydroxyconidine 161, starting from L-arabinose and applying a similar synthetic sequence (Scheme 26). 91,92 Out of eighteen glycosidases, only rat intestinal lactase (IC 50 = 418 µM) and Rhizopus sp. amyloglucosidase (IC 50 = 532 µM) were weakly inhibited by compound 161.…”

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

“…11–13 In practice, this limits the range of sugar diols that can form stable ditriflates to protected cyclic sugars where it is conformationally impossible for the initially formed monotriflate to undergo intramolecular cyclization; this approach has been used for the synthesis of azetidines. 14–19…”