Title:
PROCESS FOR PRODUCTION OF SACCHARIDE OXAZOLINE DERIVATIVES
Document Type and Number:
WIPO Patent Application WO/2003/004508
Kind Code:
A1
Abstract:
A process for production of saccharide oxazoline derivatives represented by the general formula (2), characterized by reacting an acylamino sugar represented by the general formula (1) with a metal fluoride: (1) (2) wherein X is F, Cl, Br, or I&semi R1 is H or (CH2)n−CH3 (wherein n is 0 to 5)&semi and R2, R3, R4, R5 and R6 are each independently H, N3, protected hydroxyl, protected amino, or Y−R7 (wherein Y is O, NH, or S&semi and R7 is a mono− or oligo−saccharide residue, with the proviso that when the residue bears OH, NH2 or COOH, the group(s) is protected), provided that at least one of R2 and R3 and at least one of R4 and R5 are each hydrogen.
Inventors:
SHODA SHIN-ICHIRO (JP)
FUJITA MASAYA (JP)
SUENAGA MASAKO (JP)
SAITO KENJI (JP)
FUJITA MASAYA (JP)
SUENAGA MASAKO (JP)
SAITO KENJI (JP)
Application Number:
PCT/JP2002/006575
Publication Date:
January 16, 2003
Filing Date:
June 28, 2002
Export Citation:
Assignee:
SEIKAGAKU KOGYO CO LTD (JP)
SHODA SHIN-ICHIRO (JP)
FUJITA MASAYA (JP)
SUENAGA MASAKO (JP)
SAITO KENJI (JP)
SHODA SHIN-ICHIRO (JP)
FUJITA MASAYA (JP)
SUENAGA MASAKO (JP)
SAITO KENJI (JP)
International Classes:
C07H1/00; C07H9/06; (IPC1-7): C07H9/06
Foreign References:
| JPH093088A | 1997-01-07 | |||
| JPH08245678A | 1996-09-24 | |||
| US5382665A | 1995-01-17 | |||
| JPH093088A | 1997-01-07 |
Other References:
MITCHELL M.A. ET AL.: "Synthesis of delta2-1,3-oxazolines and delta2-1,3-oxazines using potassium fluoride on alumina", SYNTHESIS, 1994, pages 675 - 677, XP002956187
SHIN-ICHIRO SHODA ET AL.: "A facile method for synthesis of 1,2-oxazoline derivative of N-acetylglucosamine promoted by potassium fluoride", CHEMISTRY LETTERS, no. 2, 5 February 2002 (2002-02-05), pages 150 - 151, XP002956188
See also references of EP 1405857A4
KOBAYASHI, SHIRO ET AL.: "A novel method for the synthesis of chitobiose via enzymatic glycosylation using a sugar oxazoline as glycosyl dono", TETRAHEDRON LETTERS, vol. 38, no. 12, 1997, pages 2111 - 2112
WONG, WAI C ET AL.: "A convenient synthesis of 2-amino-2-oxazolines and their pharmacological evaluation at cloned human alpha adrenergic receptors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 4, no. 19, 1994, pages 2317 - 2322
SHIN-ICHIRO SHODA ET AL.: "A facile method for synthesis of 1,2-oxazoline derivative of N-acetylglucosamine promoted by potassium fluoride", CHEMISTRY LETTERS, no. 2, 5 February 2002 (2002-02-05), pages 150 - 151, XP002956188
See also references of EP 1405857A4
KOBAYASHI, SHIRO ET AL.: "A novel method for the synthesis of chitobiose via enzymatic glycosylation using a sugar oxazoline as glycosyl dono", TETRAHEDRON LETTERS, vol. 38, no. 12, 1997, pages 2111 - 2112
WONG, WAI C ET AL.: "A convenient synthesis of 2-amino-2-oxazolines and their pharmacological evaluation at cloned human alpha adrenergic receptors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 4, no. 19, 1994, pages 2317 - 2322
Attorney, Agent or Firm:
Toyama, Tsutomu (4-10 Higashi Nihonbashi 3-chom, Chu-ku Tokyo, JP)
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