Synthesis of mannojirimycin derivatives

Details Synthesis of mannojirimycin derivatives Synthesis of mannojirimycin derivatives

1990-12-17

1992-08-04

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549215, 549283, 549288, C07F 702, C07D30302, C07D31102

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active

051360365

ABSTRACT:
.alpha.-Homojirimycin and 6-dpi-homojirimycin are each synthesized from 2-azido-2-deoxy-3,4:6,7-di-O- isopropylidene-D-glydero-D-talo-heptono-1,5-lactone in which the side chain acetonide is hydrolyzed to give the corresponding diol which is then protected with a silyl protecting agent to form a silyl ether. The latter compound is used as a divergent intermediate in which the piperidine ring is formed by joining the nitrogen function at C-2 to C-6 (A) with inversion of configuration at C-6 to form 6-epi-homomannojirimycin or (B) with retention of configuration at C-6 to form .alpha.-homomannojirimycin.

REFERENCES:
patent: 4357360 (1982-11-01), Light et al.
patent: 5021562 (1991-06-01), Fleet et al.
Kite et al., Tetrahedron Lett. 29, 6483-6486 (1988).
Dho et al, Tetrahedron Lett. 27, 3203-3204 (1986).

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