Synthesis of 1,4-dideoxy-1,4-imino-L-arabinitol

Details Synthesis of 1,4-dideoxy-1,4-imino-L-arabinitol Synthesis of 1,4-dideoxy-1,4-imino-L-arabinitol

1993-02-01

1994-02-15

Richter, Johann

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20712, C07D20724, C07D20736

Patent

active

052868770

ABSTRACT:
1,4-Dideoxy-1,4-imino-L-arabinitol is chemically synthesized from D-lyxonolactone by formation of the pyrrolidine ring by joining the nitrogen between C-1 and C-4 and inversion of configuration at both C-2 and C-4, with the C-3 and C-5 hydroxyl groups being protected throughout the synthesis sequence by benzylidenation. The product is preferably isolated as the hydrochloride salt and is useful as an inhibitor of .alpha.-glucosidase and human immunodeficiency virus (HIV).

REFERENCES:
patent: 4876268 (1989-10-01), Koszyk et al.
patent: 4910310 (1990-03-01), Campbell et al.
patent: 5089520 (1992-02-01), Fleet et al.
Wang et al., Tetrahedron: Asymmetry, vol. 1, No. 8, pp. 527-530 (1990).
Fleet et al., J. Chem. Soc., Perkin Trans. 1, pp. 665-666 (1989).

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