Process for producing sialic acid derivatives

Details Process for producing sialic acid derivatives Process for producing sialic acid derivatives

1989-05-16

1990-04-03

Griffin, Ronald W.

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

Organic compounds

Carbohydrates or derivatives

536 54, 536122, 536124, 536121, C07G 300, C07G 3700, C07H 2300, C07H 100

Patent

active

049140353

ABSTRACT:
The present invention provides a process for selective production of a 2-.alpha.-O-glycoside compound of sialic acid which is useful as a starting material or intermediate for medicines and biochemical reagents. The process comprises reacting an alkylthiosialic acid derivative represented by the formula [I]: ##STR1## wherein R represents an acyl group and R.sup.1 and R.sup.2 each represents a lower alkyl group with a compound having alcoholic hydroxyl group at a low temperature in a polar solvent having no hydroxyl group in the presence of a Lewis acid selected from the group consisting of methyl triflate, trimethylsilyl triflate and dimethyl(methylthio)sulfonium triflate. The present invention further provides novel compounds.

REFERENCES:
Carbohydrate Research 163 (1987), 209-225; Numata, Masaaki Sugimoto, Mamory; Kioke, Katsuya; and Ogawa, Tomoya Total Synthesis of Sialosylcerebroside, GM.sub.4.
Tetrahedron Lett., 27, 5229-5232 (1986); Okamoto, Kaoru; Kondo, Tadao; Goto, Toshio; Synthesis of (.alpha.2-9)and (.alpha.2-8) Linked Neuraminylneuraminic Acid Derivatives.sup.1.
Tetrahedron Lett., 27, 5233-5236 (1986); Okamoto, Kaoru; Kondo, Tadao; Goto, Toshio; An Effective Synthesis of .alpha.-Glycosides of N-Acetylneuraminic Acid by Use of 2.beta.-Halo-3.beta.-Hydroxy-4,7,8,9-Tetra-O-Acetyl-N-Acetylneuraminic Acid Methyl Ester.sup.1.
Tetrahedron Lett., 28, 6221-6224 (1987); Ito, Yukishige; Ogawa, Tomoya; An Effective Approach to Stereoselective Glycosylation of N-Acetylneuraminic Acid; Use of Phenylselenyl Group as a Stereocontrolling Auxiliary.
Chem. Ber., 99, 611-617 (1966); Kuhn, Richard; Lutz, Peter and MacDonald, Donald L.; Synthese Anomerer Sialinsaure-Methylketoside.
Carbohydrate Research 146 (1986) 147-153; Paulsen, Hans and von Deessen, Ulrich; Glycosidsynthese von N-AcetylNeuraminsaure mit Sekundaren Hydroxylgruppen.

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