Straightforward S–S Bond Formation via the Oxidation of S-Acetyl by Iodine in the Presence of N-Iodosuccinimide,The Journal of Organic Chemistry

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Straightforward S–S Bond Formation via the Oxidation of S-Acetyl by Iodine in the Presence of N-Iodosuccinimide
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-11-07 00:00:00 , DOI: 10.1021/acs.joc.7b02367
Jian-Tao Ge ₁ , Lang Zhou ₁ , Fu-Long Zhao ₁ , Hai Dong ₁

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Straightforward S–S bond formation via the oxidation of S-acetyl group by iodine was reported here. The reaction was further applied in the synthesis of per-O-acetylated glycosyl disulfides. These studies demonstrated great improvement in reaction rate, yield, and general convenience in the presence of N-iodosuccinimide. Furthermore, selectively deacetylated glycosyl thiols were obtained in high yields when these per-O-acetylated glycosyl disulfides were reduced with tris(2-carboxyethyl)-phosphine (TCEP). Our method supplied an efficient way to obtain both per-O-acetylated glycosyl disulfides and per-O-acetylated glycosyl thiols in which the sulfur group was located at any position.

中文翻译：

在N-碘琥珀酰亚胺存在下通过碘氧化S-乙酰直接形成S - S键。

在此报道了通过碘将S-乙酰基氧化而直接形成S - S键的方法。该反应进一步应用于过-O-乙酰化的糖基二硫化物的合成。这些研究表明，在N-碘琥珀酰亚胺的存在下，反应速率，产率和一般便利性都有了很大的提高。此外，当用三（2-羧乙基）-膦（TCEP）还原这些过-O-乙酰化的糖基二硫化物时，以高产率获得了选择性脱乙酰化的糖基硫醇。我们的方法提供了一种获得过-O-乙酰化的糖基二硫化物和过-O的有效方法-乙酰化的糖基硫醇，其中硫基位于任何位置。

更新日期：2017-11-08

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