Synthesis of mannojirimycin derivatives

Details Synthesis of mannojirimycin derivatives Synthesis of mannojirimycin derivatives

1990-12-17

1992-03-31

Shah, Mukund J.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

C07F 702

Patent

active

051010275

ABSTRACT:
.alpha.-Homojirimycin and 6-dpi-homojirimycin are each synthesized from 2 az ido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-la ctone 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 retension of configuration at C-6 to form .alpha.-homomannojirimycin.

REFERENCES:
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Rhinehart et al., J. Pharmacol. Exp. Therap. 241, 915-920 (1987).
Kite et al., Tetrahedron Lett. 29, 6483-6486 (1988).

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