Title:
METHOD FOR PRODUCING THIOLANE-SKELETON GLYCOCONJUGATE, AND THIOLANE-SKELETON GLYCOCONJUGATE
Document Type and Number:
WIPO Patent Application WO/2015/125782
Kind Code:
A1
Abstract:
A method for producing a compound represented by general formula (II) via a step for reacting a compound represented by general formula (I) with a sulfur compound, and a compound. In general formulas (I) and (II), R1 represents a hydrogen atom, alkyl group, or acyl group, R2 represents -O-R2a or a fluorine atom, and R2' represents -O-R2a, a fluorine atom, or =O. Herein, R2a represents a hydrogen atom, -CH2-R2b, or an acyl group. R2b, R3, and R5 represent a hydrogen atom, alkyl group, vinyl group, or aryl group, and X represents a leaving group. Herein, the bond from R2' to the thiolane ring represents a single bond or double bond.
Inventors:
ITO TAKAYUKI (JP)
WATANABE TORU (JP)
TAKEDA AKIRA (JP)
OKADA HIDEKI (JP)
WATANABE TORU (JP)
TAKEDA AKIRA (JP)
OKADA HIDEKI (JP)
Application Number:
PCT/JP2015/054306
Publication Date:
August 27, 2015
Filing Date:
February 17, 2015
Export Citation:
Assignee:
FUJIFILM CORP (JP)
International Classes:
C07H1/00; C07H5/10; C07H13/08; C07B53/00
Domestic Patent References:
| WO2004009020A2 | 2004-01-29 | |||
| WO2002058740A1 | 2002-08-01 | |||
| WO2001066118A1 | 2001-09-13 | |||
| WO1999043690A1 | 1999-09-02 | |||
| WO2011074484A1 | 2011-06-23 | |||
| WO2014027658A1 | 2014-02-20 |
Foreign References:
| JP2005528334A | 2005-09-22 | |||
| JP2002521318A | 2002-07-16 | |||
| JPH09249690A | 1997-09-22 | |||
| JPH0925289A | 1997-01-28 | |||
| JP2006335737A | 2006-12-14 |
Other References:
KHARE,K.N. ET AL.: "Synthesis of 4-deoxy-4- thioarabinofuranosyl disaccharides, analogs of Mycobacterial arabinogalactan", INDIAN JOURNAL OF CHEMISTRY, vol. 47 B, November 2008 (2008-11-01), pages 1748 - 1752, XP055207782
FRANCHETTI PALMARISA ET AL.: "Synthesis, Conformational Analysis, and Biological Activity of C-Thioribonucleosides Related to Tiazofurin", JOURNAL OF MEDICINAL CHEMISTRY, vol. 43, no. 7, 2000, pages 1264 - 1270, XP055221492, ISSN: 0022-2623
WIRSCHING JOERN ET AL.: "Thiosugars. Part 2. Preparation of 2,3,5-tri-O-benzyl-4-thio-L- arabino-furanosides and the corresponding 4'- thionucleoside analogs", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 3, 1999, pages 691 - 696
BELLON, L. ET AL.: "Efficient synthesis of 4-thio-D-ribofuranose and some 4'- thioribonucleosides", NUCLEOSIDES & NUCLEOTIDES, vol. 11, no. 8, 1992, pages 1467 - 1479
WIRSCHING JOERN ET AL.: "Thiosugars. X. Novel Nucleoside Analogues Derived from 4-Thio-L- lyxofuranose", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, vol. 22, no. 10, 2003, pages 1867 - 1897
WIRSCHING JOERN ET AL.: "Thiosugars. VIII. Preparation of new 4'-thio-L-lyxo pyrimidine nucleoside analogues", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, vol. 20, no. 9, 2001, pages 1625 - 1645
KIM HEA OK ET AL.: "A highly efficient synthesis of L-beta-2'-deoxy-4'-thio-1'-purine nucleosides as potential antiviral agents", PERKIN 1, vol. 9, 2000, pages 1327 - 1329, XP055221493, ISSN: 1470-4358
JEONG LAK SHIN ET AL.: "Ring contraction and rearrangement of 4-thiofuranose derivatives observed during DAST fluorination in the synthesis of L-2'-''up''-fluoro-4'-thiothymidine", TETRAHEDRON LETTERS, vol. 39, no. 29, 1998, pages 5201 - 5204, XP004162418, ISSN: 0040-4039
CLASSON BJOERN ET AL.: "Novel route to 4- thiofuranosides. Synthesis of methyl 4-thio-a- D-talofuranoside", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 6, no. 4, 1987, pages 593 - 597
FRANCHETTI PALMARISA ET AL.: "Synthesis, Conformational Analysis, and Biological Activity of C-Thioribonucleosides Related to Tiazofurin", JOURNAL OF MEDICINAL CHEMISTRY, vol. 43, no. 7, 2000, pages 1264 - 1270, XP055221492, ISSN: 0022-2623
WIRSCHING JOERN ET AL.: "Thiosugars. Part 2. Preparation of 2,3,5-tri-O-benzyl-4-thio-L- arabino-furanosides and the corresponding 4'- thionucleoside analogs", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 3, 1999, pages 691 - 696
BELLON, L. ET AL.: "Efficient synthesis of 4-thio-D-ribofuranose and some 4'- thioribonucleosides", NUCLEOSIDES & NUCLEOTIDES, vol. 11, no. 8, 1992, pages 1467 - 1479
WIRSCHING JOERN ET AL.: "Thiosugars. X. Novel Nucleoside Analogues Derived from 4-Thio-L- lyxofuranose", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, vol. 22, no. 10, 2003, pages 1867 - 1897
WIRSCHING JOERN ET AL.: "Thiosugars. VIII. Preparation of new 4'-thio-L-lyxo pyrimidine nucleoside analogues", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, vol. 20, no. 9, 2001, pages 1625 - 1645
KIM HEA OK ET AL.: "A highly efficient synthesis of L-beta-2'-deoxy-4'-thio-1'-purine nucleosides as potential antiviral agents", PERKIN 1, vol. 9, 2000, pages 1327 - 1329, XP055221493, ISSN: 1470-4358
JEONG LAK SHIN ET AL.: "Ring contraction and rearrangement of 4-thiofuranose derivatives observed during DAST fluorination in the synthesis of L-2'-''up''-fluoro-4'-thiothymidine", TETRAHEDRON LETTERS, vol. 39, no. 29, 1998, pages 5201 - 5204, XP004162418, ISSN: 0040-4039
CLASSON BJOERN ET AL.: "Novel route to 4- thiofuranosides. Synthesis of methyl 4-thio-a- D-talofuranoside", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 6, no. 4, 1987, pages 593 - 597
Attorney, Agent or Firm:
IIDA, Toshizo et al. (JP)
Toshizo Iida (JP)
Toshizo Iida (JP)
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