- Alkyl sulfinates: Formal nucleophiles for synthesizing TosMIC analogs
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Alkyl sulfinates function as formal nucleophiles in Mannich-type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two-step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.
- Lujan-Montelongo, J. Armando,Estevez, Angel Ojeda,Fleming, Fraser F.
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supporting information
p. 1602 - 1605
(2015/03/04)
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- COMPOSITION, SYNTHESIS, AND USE OF NEW ARYLSULFONYL ISONITRILES
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This invention relates to novel isonitriles, including arylsulfonyl isonitriles, and methods for their synthesis. The isonitriles include a conjugated ring system. The structure is designed with the flexibility to have multiple substitution patterns. The isonitriles may be used in applications including, but not limited to, pharmaceutical compositions.
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Paragraph 0171
(2015/09/23)
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- Trimethoxyphenylthio as a highly labile replacement for tert-butylthio cysteine protection in fmoc solid phase synthesis
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Trimethoxyphenylthio (S-Tmp) is described as a novel cysteine protecting group in Fmoc solid phase peptide synthesis replacing the difficult to remove tert-butylthio. S-Tmp and dimethoxyphenylthio (S-Dmp) were successfully used for cysteine protection in a variety of peptides. Moreover, both groups can be removed in 5 min with mild reducing agents. S-Tmp is recommended for cysteine protection, as it yields crude peptides of high purity.
- Postma, Tobias M.,Albericio, Fernando,Giraud, Matthieu
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supporting information
p. 5468 - 5471,4
(2012/12/13)
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- Trimethoxyphenylthio as a highly labile replacement for tert-butylthio cysteine protection in fmoc solid phase synthesis
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Trimethoxyphenylthio (S-Tmp) is described as a novel cysteine protecting group in Fmoc solid phase peptide synthesis replacing the difficult to remove tert-butylthio. S-Tmp and dimethoxyphenylthio (S-Dmp) were successfully used for cysteine protection in a variety of peptides. Moreover, both groups can be removed in 5 min with mild reducing agents. S-Tmp is recommended for cysteine protection, as it yields crude peptides of high purity.
- Postma, Tobias M.,Giraud, Matthieu,Albericio, Fernando
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supporting information
p. 5468 - 5471
(2013/01/15)
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- Bis(2,6-dimethoxyphenyl) sulfide, selenide and telluride, and their derivatives
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2,6-Dimethoxyphenyl derivatives of sulfur, selenium, and tellurium, such as ΦEEΦ, Φ2E, ΦSeH, [MeΦ2E]X (X = MeSO4, ClO4), Φ2EO · xH2O, [Φ2EOH]ClO4, [Φ2EOR]Cl
- Wada, Masanori,Nobuki, Shin-Ichi,Tenkyuu, Yoshinori,Natsume, Satoko,Asahara, Masahiro,Erabi, Tatsuo
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p. 282 - 289
(2007/10/03)
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- Two-step synthesis of triarylmetals (As, Sb, Bi) starting from the metal oxides and 2,6-dimethoxybenzenethiol
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Reported here is a new synthetic method of triarylmetals MAr3 (M = As, Sb, Bi). It is composed of two-step reactions starting from the metal oxides: (1) A reaction of the metal oxide with 2,6-dimethoxybenzenethiol ΦSH [Φ = 2,6-(MeO)2C6H3] in the presence of acid to give the thiolatometals M(SΦ)3, and (2) A reaction of M(SΦ)3 with organolithium reagent LiAr to give MAr3 (Ar = Ph, 4-MeC6H4, 4-Me2NC6H4, Φ). Since ΦSH is odorless and crystalline, most of it can be recovered after the reactions without difficulty for repeated usages. The intermediates M(SΦ)3 are also crystalline and inert against hydrolysis.
- Wada, Masanori,Natsume, Satoko,Suzuki, Shinobu,Uo, Akira,Nakamura, Michiaki,Hayase, Shuichi,Erabi, Tatsuo
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p. 223 - 227
(2007/10/03)
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