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Patent Searching and Data


Title:
NEW PREPARATION OF NOJIRIMYCIN AND RELATED COMPOUND
Document Type and Number:
Japanese Patent JPH0418072
Kind Code:
A
Abstract:

PURPOSE: To effectively prepare the subject compound, by converting 1,2-O- isopropylidene-5-oxo-α-D-glucuronolactone hydrate into its oxime, catalytically hydrogenating the same, reducing the product by a hydride reducing agent, and reacting the reduced product with sulfur dioxide.

CONSTITUTION: A compound of formula I is reacted with O-(1-4C alkyl) hydroxylamine, O-benzyhydroxylamine or O-trimethylsilylhydroxylamine, to form its corresponding oxime of formula II. Then the oxime is catalytically hydrogenated in the presence of an amine protective reagent by using palladium on carbon, to form a protected amine lactone of formula III (APG is an amine protective group), and the same is reduced by a hydride reducing agent to form 5-amino-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose of formula IV. The compound is treated with a saturated aqueous sulfur dioxide to form 1- dioxynojirimycin-1-sulfonic acid, and then the compound is hydrogenated on Raney nickel to form 1-deoxynojirimycin.


Inventors:
PIITAA BIAJIO ANZEBENO
RAURA JIIN KURIIMAA
Application Number:
JP41170890A
Publication Date:
January 22, 1992
Filing Date:
December 19, 1990
Export Citation:
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Assignee:
MERRELL DOW PHARMA
International Classes:
C07D211/44; A61K31/445; A61P3/08; C07H5/04; C07H9/04; C07H11/00; C07H13/12; (IPC1-7): C07D211/44
Attorney, Agent or Firm:
Yataro Sasai (1 person outside)