Synthesis of chiral pyrrolidine and piperidine glycosidase inhib

Details Synthesis of chiral pyrrolidine and piperidine glycosidase inhib Synthesis of chiral pyrrolidine and piperidine glycosidase inhib

1990-01-22

1991-05-07

Brust, Joseph Paul

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546242, 548531, 548532, 548533, 548556, C07D20712, C07D21122

Patent

active

050138421

ABSTRACT:
There is disclosed a novel method for the syntheses of chiral pyrrolidines and piperidines by the intramolecular ring closure of anomeric mixtures of 4-amino- and 5-amino-2-trifluoromethanesulfonates of methyl furanosides. The novel method preferably provides for the efficient syntheses from diacetone glucose of 1,4-dideoxy-1,4-imino-D-arabinitol--known as DAB1, (2S,3R,4R)-3,4-dihydroxyproline, fagomine [1,5-imino-1,2,5-trideoxy-D-arabino-hexitol], and (2S,3R,4R)-3,4-dihydroxypipecolic acid by intramolecular nucleophilic displacement by an amino function of 2-O-trifluoromethanesulphonates of anomeric mixtures of methyl furanosides.

REFERENCES:
patent: 4469875 (1984-09-01), Busker et al.
patent: 4611058 (1986-09-01), Koebernick
patent: 4894388 (1990-01-01), Fleet
patent: 4937357 (1990-06-01), Koszyk et al.
Bashyal et al., Tetrahedron Letters, 27, pp. 3205-3208, (1986).
Austin et al., Tetrahedron, 43, pp. 3095-3108, (1987).
Bashyal et al., Tetrahedron, 43, pp. 423-430, (1987).
Bashyal et al., Tetrahedron, 43, pp. 415-422, (1987).
Tyms et al., Lancet, pp. 1025-1026 (1987).
Fleet et al., Febs Lett. 237, 128-132 (1988).
Fleet et al., Tetrahedron Lett. 26, 3127-3130 (1985).
Fleet and Smith, Tetrahedron 42, 5685-5692 (1986).
Fleet et al., Tetrahedron 43, 979-990 (1987).
Ziegler et al., Angew. Chem. Int. Ed. Engl. 27, 716 (1988).
von der Osten et al., J. Am. Chem. Soc. 111, 3924-3927 (1989).

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