METHOD FOR PRODUCING D-MANNOSAMINE DERIVATIVE

Title:

METHOD FOR PRODUCING D-MANNOSAMINE DERIVATIVE

Document Type and Number:

Japanese Patent JP3703509

Kind Code:

B2

Abstract:

PURPOSE: To obtain a D-mannosamine derivative useful as an intermediate for neuraminic acid by protecting the hydroxyl group of a specific talopyranose compound, treating the protected compound with a base, protecting the produced hydroxyl group, deprotecting the first hydroxyl group, oxidizing the product, treating the oxidation product with hydroxyamine and subsequently reducing the treated product.
CONSTITUTION: The method for producing the D-mannosamine deirvative of formula V used as the precursor of D-mannosamine useful as a synthetic intermediate for neuraminic acid comprises protecting the hydroxyl group of 1, 6:3,4- dianhydro-β-D-talopyranose of formula I with a 1-ethoxyethyl group, etc., treating the protected product with a base, protecting the hydroxyl group of the produced β-D-mannopyranose derivative of formula II (R2 is the hydroxyl group-protecting group) with a phenylmethyl group, etc., removing the hydroxyl group-protecting group of R2 from the protected compound, oxidizing the produced compound of formula III (R1 is the hydroxyl group-protecting group), treating the oxidation product with hydroxyamine or its derivative, and subsequently reducing the produced oxime compound of formula IV.

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Inventors:

Takashi Takahashi
Haruo Yamada

Application Number:

JP22032794A

Publication Date:

October 05, 2005

Filing Date:

September 14, 1994

Export Citation:

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Assignee:

KURARAY CO.,LTD.

International Classes:

C07H1/00; C07H3/10; C07H5/04; C07H5/06; (IPC1-7): C07H5/04; C07H1/00; C07H5/06

Domestic Patent References:

JP5448778A

Other References:

A. K. CHATTERJEE, D. HORTON, J. S. JEWELL, KERSTIN D. PHILIPS,SYNTHESIS OF 1,6-ANHYDRO DEDRIVATIVES OF 2-AMINO-2-DEOXY-β-D-TALOPYRANOSE AND 4-AMINO-4-DEOXY-β-D-TALOPYRANOSE,Carbohydrate Research,1968年,7,173-179

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