Synthesis of nojirimycin derivatives

Details Synthesis of nojirimycin derivatives Synthesis of nojirimycin derivatives

1989-10-12

1991-02-19

Lee, Mary C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D21140

Patent

active

049945726

ABSTRACT:
Nojirimycin .delta.-lactam and deoxynojirimycin are each synthesized from 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-idofuranose as a divergent intermediate by a method which comprises formation of the piperidine ring by connection of nitrogen between C-1 and C-5 with inversion of configuration at C-5 to form nojirimycin .delta.-lactam or between C-2 and C-6 with inversion of configuration at C-2.

REFERENCES:
patent: 4849430 (1989-07-01), Fleet et al.
Bernotas & Ganem, Tetrahedron Lett. 26, 1123 (1985).
Saeki & Ohki et al., Chem. Pharm. Bull. 16, 2477 (1968).
Schmidt et al., Liebigs Ann. Chem. 1989, p. 423.
Inouye et al., Tetrahedron 24, 2125-2144 (1968).
Whistler & Gramera, J. Org. Chem. 29, 2609 (1964).
Nayak & Whistler, Ibid. 33, 3582 (1968).
Fleet & Smith, Tetrahedron 43, 971-978 (1987).
Fleet et al. Ibid. 43, 979-990 (1987).
Fleet et al, Tetrahedron 45, 327 (1989).

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