Oligosialyl-1,2-dialkyl-sn-glycerols and synthetic intermediates

Details Oligosialyl-1,2-dialkyl-sn-glycerols and synthetic intermediates Oligosialyl-1,2-dialkyl-sn-glycerols and synthetic intermediates

1993-09-07

1995-11-28

Robinson, Douglas W.

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

Organic compounds

Carbohydrates or derivatives

536 175, 536 185, C07H 506

Patent

active

054709628

ABSTRACT:
An oligosialyl-1,2-dialkyl-sn-glycerol represented by the following formula (I): ##STR1## wherein each R.sup.1 independently represents a group selected from the group consisting of a hydrogen atom and alkali metal atoms, each R.sup.2 independently represents an alkyl group having 14 to 18 carbon atoms, Ac represents an acetyl group, and n represents an integer of from 0 to 20, and synthetic intermediates for their preparation useful as an immuno-stimulating agent, an antitumor agent, and a diagnostic and therapeutic agent for cancers.

REFERENCES:
patent: 4694076 (1987-09-01), Ogawa et al.
Tetrahedron, vol. 46, No. 1, 1990 Tomoya Ogawa et al: "Highly Stereoselective Glycosylation of Sialic Acid Aided by Stereocontrolling Auxiliaries", pp. 89-102.
J. Am. Chem. Soc., 1989, 111, Yukishige Ito et al: "Highly Stereoselective Synthesis of Ganglioside GD.sub.3.sup.1 ", pp. 8508-8510.
Journal of Biological Chemistry, vol. 240, No. 1, Jan. 1965, Erich Baer et al: "Phosphonolipids--Synthesis of Dialkyl L-.alpha.-Glyceryl-(2-Aminoethyl)Phosponates", pp. 44-48.
Biochemistry, vol. 2, No. 2, 1963, M. Kates et al: "Aliphatic Diether Analogs of Glyceride-Derived Lipids--Synthesis of D-.alpha.,.beta.-Dialkyl Glyceryl Ethers", pp. 394-397.
Agric. Biol. Chem., vol. 46, No. 1, 1982, Tomoya Ogawa et al: "Synthesis of 3-O-Glycosyl-1,2-Di-O-Tetradecyl-sn-Glycerol", pp. 255-262.
Tetrahedron Letters, vol. 29, No. 32, 1988, Yukishige Ito et al: "Highly Stereoselective Glycosylation of N-Acetylneuraminic Acid Aided by a Phenylthio Substituent as a Stereocontrolling Auxiliary", pp. 3987-3990.
J. Org. Chem., vol. 57, 1992, Yukishige Ito: "Studies Directed Toward the Synthesis of Polysialogang-Liosides: The Regio-and Stereocontrolled Synthesis of Rationally Designed Fragments of the Tetrasialoganglioside GQ.sub.1b ", pp. 1821-1831.
A. L. Lehninger "Biochemistry" second edition, Worth Publishers, Inc., New York, 1975, p. 287.

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