Intermediates for incorporation of tetrahydroxypipecolic acid analogues of α- and β-d-mannopyranose into combinatorial libraries: unexpected nanomolar-range hexosaminidase inhibitors. Synthesis of α- and β-homomannojirimycin (cas 127995-29-3)

Add time:08/23/2019    Source:sciencedirect.com

Homoazasugars have the distinction as a class of natural products in that most of them have been synthesised before they were isolated. Syntheses of α-1 and β-homomannojirimycin 2 rely on the stereoselective and chemoselective sodium cyanoborohydride reduction of a [2.2.2] bicyclic imino lactone (6) to give a single [2.2.2] bicyclic amino-lactone (7). Methanolysis of 7 under basic conditions is accompanied by efficient epimerisation of the first formed α-amino-ester (8) to the more stable β-amino-ester (9) in which the 2,6-substitutents are equatorial. Both 7 and 9 are suitable intermediates for the incorporation of tetrahydroxypipecolic acid derivatives into combinatorial libraries containing α- and β-C-glycosyl analogues of aza-d-mannopyranose, respectively. Methylamides derived from 7 and 9 are shown to be specific and potent inhibitors of two β-N-acetylglucosaminidases but have no effect on an α-N-acetylgalactosaminidase. The synthesis of α-14 and β-17 manno-pipecolic acids is also reported.

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