696-63-9Relevant articles and documents
Spontaneous substitution of azulene-derived benzylic alcohols by thiols and its application to labeling/protection of biothiols
Jin, Yu,Akagawa, Kengo,Kudo, Kazuaki
supporting information, (2021/02/27)
By mixing guaiazulene-3-methanol derivatives and thiols at room temperature, benzylic substitution of the alcohol proceeded to yield the corresponding sulfide. Because of the blue color of the guaiazulene derivative, this spontaneous reaction was used for labeling of paper-immobilized biothiols. By treatment with tris(2-carboxyethyl)phosphine hydrochloride, the guaiazulene-3-ylmethyl part of the sulfide could be removed and the original thiol recovered. Based on these findings, a guaiazulene-3-methanol derivative was used as a protective group for the synthesis of cysteine derivatives.
Copper-Catalyzed Direct Synthesis of Aryl Thiols from Aryl Iodides Using Sodium Sulfide Aided by Catalytic 1,2-Ethanedithiol
Xue, Hongyu,Jing, Bing,Liu, Shasha,Chae, Junghyun,Liu, Yajun
, p. 2272 - 2276 (2017/10/06)
A copper-catalyzed direct and effective synthesis of aryl thiols from aryl iodides using readily available Na 2 S·9H 2 O and 1,2-ethanedithiol was described. A variety of aryl thiols were readily obtained in yields of 76-99%. In this protocol, Na 2 S·9H 2 O was used as ultimate sulfur source, and 1,2-ethanedithiol functioned as an indispensable catalytic reagent.
Tris(3-hydroxypropyl)phosphine (THPP): A mild, air-stable reagent for the rapid, reductive cleavage of small-molecule disulfides
McNulty, James,Krishnamoorthy, Venkatesan,Amoroso, Dino,Moser, Michael
, p. 4114 - 4117 (2015/11/03)
Tris(3-hydroxypropyl)phosphine (THPP) is demonstrated to be a versatile, water-soluble and air-stable reducing agent, allowing for the rapid, irreversible reductive cleavage of disulfide bonds in both aqueous and buffered aqueous-organic media. The reagent shows exceptional stability at biological pH under which condition it permits the rapid reduction of a wide range of differentially functionalized small-molecule disulfides.