30453-20-4Relevant articles and documents
Design and synthesis of an aminobenzo-15-crown-5-labeled estradiol tethered with disulfide linkage
Harusawa, Shinya,Yoshida, Kazufumi,Kojima, Chihiro,Araki, Lisa,Kurihara, Takushi
, p. 11911 - 11922 (2004)
A novel measuring method (electroimmunoassay) of 17β-estradiol (E 2) in urine or blood was proposed on the basis of a competition between E2 and a labeled E2 against an immobilizing antibody. To evaluate the principle, 3-{4-[17β-hydroxy-1,3,5(10)- estratrien-3-yloxy]butyldisulfanyl}-N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14, 17-pentaoxabenzocyclopentadecen-2-yl) succinamic acid (1) was designed and synthesized as a novel aminobenzo-15-crown-5-containing E2 tethered with disulfide linkage. Two thiol-intermediates 5b and 19c were efficiently synthesized from mercaptosuccinic acid 7 and 4,4′-dithiodibutyric acid 12, respectively. Formations of disulfide linkages from less reactive thiols were examined and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) could be employed for the formation of an unsymmetrical disulfide 20c from 5b and 19c. Then, removal of TMS- and allyl-protecting groups in 20c successfully afforded the crown ether-containing E2 1. Graphical Abstract
Efficient synthesis of unsymmetrical disulfides
Vandavasi, Jaya Kishore,Hu, Wan-Ping,Chen, Chung-Yu,Wang, Jeh-Jeng
experimental part, p. 8895 - 8901 (2011/11/30)
A novel way of synthesizing unsymmetrical disulfides from thiols with DDQ is presented here. This procedure ran in a straightforward manner to give high product yields. Unsymmetrical disulfides were directly synthesized from the corresponding mixture of thiols in equimolar amounts under mild conditions.
Oxidative Cleavage and Cyclization of Disulfide Carboxylic Acids and Alcohols by Aqueous Iodine: A Facile Route to Five-Membered Ring Sultines
Doi, Joyce Takahashi,Luehr, Gary W.,Musker, W. Kenneth
, p. 5716 - 5719 (2007/10/02)
The kinetics and mechanism of the oxidative cleavage by aqueous iodine of disulfide carboxylic acids and alcohols are presented.There is evidence for intramolecular interaction of the oxygen nucleophiles.The sole product of the iodine oxidation of 3,3'-dithiodipropanol is the sultine 1,2-oxathiolane 2-oxide, which is formed after the rate-determining step, apparently via rapid cyclization of the sulfenyl iodide.The anchimeric assistance provided by the neighboring carboxylate group in the reaction of 3,3'-dithiodipropanoic acid is responsible for the pH profile of the rate of oxidative cleavage.At a given pH, the rate law for the reaction is -d/dt = kI3->(0.0905->-1 + 0.0019->-2).The inverse second term in iodide ion not has been observed previously in kinetic studies of disulfide reactions and is interpreted as evidence for a disulfide-iodonium complex.
