Title:
NOVEL DEALKOXYPHENYLATION REACTION
Document Type and Number:
WIPO Patent Application WO/2022/191312
Kind Code:
A1
Abstract:
[Abstract] [Problem] To provide a method for producing a dealkoxyphenylation product with high yield from a substrate, e.g., a sugar, which is bonded to an alkoxyphenyl group through an oxygen atom. [Solution] A substrate that is bonded to a phenyl group substituted by a C1 to C5 alkoxy group at a para- or ortho-position through an oxygen atom is reacted with a λ3-iodane in a fluorous alcohol and water, whereby a dealkoxyphenylation product can be obtained with high yield under mild conditions.
Inventors:
UEDA TSUYOSHI (JP)
NAKAMURA TATSUYA (JP)
NAKAMURA TATSUYA (JP)
Application Number:
PCT/JP2022/010839
Publication Date:
September 15, 2022
Filing Date:
March 11, 2022
Export Citation:
Assignee:
DAIICHI SANKYO CO LTD (JP)
International Classes:
C07B51/00; A61K47/54; C07C29/00; C07C33/22; C07D207/30; C07D209/04; C07D213/30; C07D215/14; C07D233/54; C07D239/26; C07D251/16; C07D275/02; C07D277/24; C07D307/42; C07D309/06; C07D333/16; C07D335/02; C07D473/00; C07H3/02; C07H3/04; C07H3/06; C07H5/06; C08B37/00
Domestic Patent References:
| WO2007128463A1 | 2007-11-15 | |||
| WO2010047318A1 | 2010-04-29 |
Foreign References:
| JP2014031352A | 2014-02-20 |
Other References:
OCHIAI, MASAHITO: "Utilization of iodine resources. Synthesis and reaction of hypervalent organic iodine compounds", TCI MAIL, TOKYO KASEI KOGYO CO., JP, no. 104, 30 September 1999 (1999-09-30), JP , pages 2 - 11, XP009515036
HAMADA SHOHEI, SUGIMOTO KOICHI, ELBORAY ELGHAREEB E., KAWABATA TAKEO, FURUTA TAKUMI: "Chemoselective Oxidation of p -Methoxybenzyl Ethers by an Electronically Tuned Nitroxyl Radical Catalyst", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 22, no. 14, 17 July 2020 (2020-07-17), US , pages 5486 - 5490, XP055966291, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.0c01839
JAMES R. PORTER, TRAVERSE JOHN F., HOVEYDA AMIR H., SNAPPER MARC L.: "Three-Component Catalytic Asymmetric Synthesis of Aliphatic Amines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 123, no. 42, 1 October 2001 (2001-10-01), pages 10409 - 10410, XP055006439, ISSN: 00027863, DOI: 10.1021/ja0118744
MATSUZAKI, Y.ITO, Y.NAKAHARA, Y.OGAWA, T., TETRAHEDRON LETT, vol. 34, 1993, pages 1061
FUKUYAMA, T.LAIRD, A. A.HOTCHKISS, L. M., TETRAHEDRON LETT, vol. 26, 1985, pages 6291
IACOBUCCI, S.FILIPPOVA, N.ALARCAO, M., CARBOHYDRATE RES, vol. 277, 1995, pages 321
ZHANG, Z.MAGNUSSON, G., CARBOHYDRATE RES, vol. 925, 1996, pages 41
HAMADA SHOHEI, SUGIMOTO KOICHI, ELBORAY ELGHAREEB E., KAWABATA TAKEO, FURUTA TAKUMI: "Chemoselective Oxidation of p -Methoxybenzyl Ethers by an Electronically Tuned Nitroxyl Radical Catalyst", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 22, no. 14, 17 July 2020 (2020-07-17), US , pages 5486 - 5490, XP055966291, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.0c01839
JAMES R. PORTER, TRAVERSE JOHN F., HOVEYDA AMIR H., SNAPPER MARC L.: "Three-Component Catalytic Asymmetric Synthesis of Aliphatic Amines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 123, no. 42, 1 October 2001 (2001-10-01), pages 10409 - 10410, XP055006439, ISSN: 00027863, DOI: 10.1021/ja0118744
MATSUZAKI, Y.ITO, Y.NAKAHARA, Y.OGAWA, T., TETRAHEDRON LETT, vol. 34, 1993, pages 1061
FUKUYAMA, T.LAIRD, A. A.HOTCHKISS, L. M., TETRAHEDRON LETT, vol. 26, 1985, pages 6291
IACOBUCCI, S.FILIPPOVA, N.ALARCAO, M., CARBOHYDRATE RES, vol. 277, 1995, pages 321
ZHANG, Z.MAGNUSSON, G., CARBOHYDRATE RES, vol. 925, 1996, pages 41
Attorney, Agent or Firm:
KAWAGUTI & PARTNERS (JP)
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