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Photodissociable protective group

外国特許コード F120006101
整理番号 S2008-0204
掲載日 2012年1月6日
出願国 アメリカ合衆国
出願番号 92159709
公報番号 20110028738
公報番号 8222429
出願日 平成21年1月8日(2009.1.8)
公報発行日 平成23年2月3日(2011.2.3)
公報発行日 平成24年7月17日(2012.7.17)
国際出願番号 JP2009050102
国際公開番号 WO2009113322
国際出願日 平成21年1月8日(2009.1.8)
国際公開日 平成21年9月17日(2009.9.17)
優先権データ
  • 特願2008-061795 (2008.3.11) JP
  • 2009WO-JP50102 (2009.1.8) WO
発明の名称 (英語) Photodissociable protective group
発明の概要(英語) (US8222429)
The present invention provides a photolabile protecting group that can be removed by light irradiation under mild conditions.
More specifically, the present invention provides a method comprising protecting a reactive functional group (e.g., a hydroxyl group, amino group, carboxyl group, carbonyl group, phosphodiester group, etc.) by the photolabile protecting group, and then removing the photolabile protecting group simply by light irradiation under neutral conditions.
The present invention relates to a compound represented by Formula (3): wherein Ar1 is an optionally substituted aromatic or heteroaromatic ring, Ar2 is an optionally substituted aryl or heteroaryl group, X is a leaving group, and n is an integer of 1 or 2; and a method of protecting and deprotecting an amino group etc. using the compound.
特許請求の範囲(英語) [claim1]
1. A compound represented by Formula (3):
wherein Ar1 is an optionally substituted aromatic or heteroaromatic ring, Ar2 is an optionally substituted aryl or heteroaryl group, X is a leaving group, and n is an integer of 1 or 2,
wherein the aromatic or heteroaromatic ring of Ar1 is selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a dibenzo[b,d]furan ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring;
wherein the optionally substituted aromatic ring Ar1 and/or the optionally substituted aryl group Ar2 has one to three substituents selected from the group consisting of an alkyl group, a haloalkyl group, an alkoxy group, a dialkylamino group, a halogen atom, a cyano group, and a nitro group; and
wherein the leaving group X is selected from the group consisting of a halogen atom, an imidazolyl group, and a pentafluorophenyl group.
[claim2]
2. A method of producing a compound represented by Formula (3):
wherein Ar1 is an optionally substituted aromatic or heteroaromatic ring, Ar2 is an optionally substituted aryl or heteroaryl group, X is a leaving group, and n is an integer of 1 or 2,
wherein the aromatic or heteroaromatic ring of Ar1 is selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a dibenzo[b,d]furan ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring;
wherein the optionally substituted aromatic ring Ar1 and/or the optionally substituted aryl group Ar2 has one to three substituents selected from the group consisting of an alkyl group, a haloalkyl group, an alkoxy group, a dialkylamino group, a halogen atom, a cyano group, and a nitro group;
wherein the leaving group X is selected from the group consisting of a halogen atom, an imidazolyl group, and a pentafluorophenyl group;
wherein the method comprises reacting a compound represented by Formula (1):
wherein Ar1, Ar2, and n are as defined above, with a compound represented by Formula (2):
wherein X are the same or different, and each represent the leaving group as defined above, or an equivalent thereof.
[claim3]
3. A method of protecting an amino group or hydroxyl group, comprising reacting the amino group or hydroxyl group with a compound represented by Formula (3):
wherein Ar1 is an optionally substituted aromatic or heteroaromatic ring, Ar2 is an optionally substituted aryl or heteroaryl group, X is a leaving group, and n is an integer of 1 or 2,
wherein the aromatic or heteroaromatic ring of Ar1 is selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a dibenzo[b,d]furan ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring;
wherein the optionally substituted aromatic ring Ar1 and/or the optionally substituted aryl group Ar2 has one to three substituents selected from the group consisting of an alkyl group, a haloalkyl group, an alkoxy group, a dialkylamino group, a halogen atom, a cyano group, and a nitro group; and
wherein the leaving group X is selected from the group consisting of a halogen atom, an imidazolyl group, and a pentafluorophenyl group.
  • 発明者/出願人(英語)
  • SUGAWARA KAZUKI
  • GOSYO YOSHINORI
  • NARA INSTITUTE OF SCIENCE AND TECHNOLOGY
国際特許分類(IPC)
米国特許分類/主・副
  • C07D335/06
  • C07D409/04
  • C07F009/6553P60
  • C07H013/12
  • C07J033/00
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