Process for the stereoselective preparation of .beta.-fucopyrano

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 187, 536 553, 536115, 536117, 536124, C07H 1104, C07H 100

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053712030

ABSTRACT:
The invention relates to a process for the stereoselective preparation of .beta.-L-fucopyranosyl phosphates via the trichloroacetimidates of protected L-fucose and the synthesis and purification of very pure GDP-fucose from the .beta.-L-fucopyranosyl phosphates.

REFERENCES:
patent: 4952683 (1990-08-01), Tschannen et al.
patent: 4987271 (1991-01-01), Watabe et al.
Chemical Abstracts, vol. 96, No. 23, issued 7 Jun. 1982, Asahi Chemical Industry Co., Ltd. "Production of Guanosine Diphosphate Fucose with Microorganisms," See page 522, Col. 2, abstract No. 197918s, 30 Jan. 1982, Appl. 80/92, 782, 09 Jul. 1980; 4 pages.
Chemical Abstracts, vol. 100, No. 21, issued 21 May 1984, Yamamoto et al, "Preparation of GDP-L-fucose by using microbial enzymes," See page 497 Col. 1, abstract No. 173093u, Biol. Chem. 1984, 4813h 823-4 (Eng).
Chemical Abstracts, vol. 113, No. 23, issued 3 Dec. 1990, Gokhale et al, "Chemical Synthesis of GDP-fucose analogs and their utilization by the Lewis .alpha.(1-34) Fucosyltransferase." See page 828, col. 2, abstract No. 212565q, Can. J. Chem. 1990, 68(7), 1063-71 (Eng).
Chemical Abstracts, vol. 115, No. 3, issued 22 Jul. 1991, Tochikura et al, "Guanosine Diphosphate L-Fucose and its Manufacture with Klebsiella Pneumoniae," see page 635, col. 1, abstract No. 27718v, 02 Nov. 1990, Appl. 89/89, 565, 07 Apr. 1989; 4 pages.
Chemical Abstracts, vol. 78, No. 17, issued 30 Apr. 1973, Prihar et al, "Chemical Synthesis of .beta.-L-Furopyranosyl Phosphate and .beta.-L-Rhamnopyranosyl Phosphate" see page 522, col. 1, abstract No. 111693h, Biochemistry 1973, 12(5), 997-1002 (Eng).
Chemical Abstracts, vol. 84, No. 13, issued 29. Mar. 1976, Prohaska et al, "simple and efficient method for the preparation of GDP-fucose." see page 240, col. 2, abstract No. 86417k, Anal. Biochem. 1975, 69(2), 536-44 (Eng).
Chemical Abstracts, vol. 88, No. 17, issued 24 Apr. 1978, Prihar et al, "Synthesis of .beta.-L-fucopyranosyl Phosphate and L-Fucofuranosyl phosphates by the MacDonald Procedure." See page 581, col. 2, abstract No. 121561j, Carbohydr. Res. 1977, 56(2), 315-24 (Eng).
Chemical Abstracts, vol. 95, No. 19, issued 9 Nov. 1981, Nunez, et al, "the Synthesis and Characterization of .alpha.-and .beta.-L-Fucopyranosyl Phosphates and GDP-Fucose." See page 794, col. 2, abstract No. 169680u, Can. J. Chem. 1981, 59(14), 2086-95 (Eng).
H. Nunez et al., "The synthesis and characterization of .alpha.-and .beta.-L-fucopyranosyl . . . ", Can. J. Chem. Vol. 59, pp. 2086-2095 (9181).

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