A Simple Synthesis of Nβ-Fmoc/Z-Amino Alkyl Thiols and their use in the Synthesis of Nβ-Fmoc/Z-Amino Alkyl Sulfonic Acids

Abstract

A simple and efficient protocol for the synthesis of N bFmoc/Z-amino alkyl thiols is described. The approach uses sodium pyrosulfite-mediated hydrolysis of isothiouronium salts resulting from the reaction between N-protected aminoalkyl iodides and thiourea. N-Protected taurines were prepared through performic acid oxidation of the thiols and the products were further utilized for the synthesis of dipeptidosulfonamides.

Synthesis of Nβ-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol

“…We had described an efficient protocol for the synthesis of N-protected amino alkyl thiols and demonstrated their multiple applications for the construction of sulfur-containing peptidomimetics . In the proposed protocol, the sulfonyl methyl formamides were synthesized from corresponding N-protected amino alkyl thiols, which were prepared from our previously reported protocol .…”

A Simple Approach for the Synthesis of Thio-, Dithio- and Selenothiocarbamate-Tethered Peptidomimetics

“…Briefly, N-protected amino alkyl iodides were prepared under Mitsunobu condition, which were then treated with thiourea followed by mild hydrolysis with Na 2 S 2 O 5 . 23 To prepare dipeptidomimetics of the type 5a-c (Scheme 1), reaction of methyl isocyano valinate 2a with equimolar amount of N-Fmoc-Ala-ψ-[CH 2 SH] 1a without using any base was carried out in CH 2 Cl 2 . Interestingly, thiocarbamate 5a was obtained in 68% yield when the reaction was stirred at room temperature for five hours ( Table 1, entry 1) and in 72% yield when the reaction was performed at 65 ºC for three hours ( Table 1, entry 2).…”

“…Synlett 2012,23,[1516][1517][1518][1519][1520][1521][1522] © Georg Thieme Verlag Stuttgart • New York…”

“…© Georg Thieme Verlag Stuttgart • New YorkSynlett 2012,23,[1516][1517][1518][1519][1520][1521][1522] …”

An efficient one-pot access to trithiocarbonate-tethered peptidomimetics

“…This intermediate was hydrolyzed with aqueous sodium pyrosulfite to afford corresponding thiol. 26 On the other hand, a-bromo esters 2 were prepared through diazotization of the corresponding amino acid in the presence of KBr followed by esterification using CH 3 OH and SOCl 2 . 27 Having the amino acid derived halide and thiol components in hand, we next proceeded toward the synthesis of title molecules.…”