4498-99-1Relevant articles and documents
Boc-S-methylbenzyl-(S)-2-amino-6-mercaptohexanoic acid: Preparation and application to the synthesis of a large cyclic disulfide peptide
Adeva, Alberto
, p. 3885 - 3888 (1995)
A derivative of 2-amino-6-mercaptohexanoic acid (Amh) suitable for Boc solid phase synthesis has been prepared by conversion of the ε-NH2 group of lysine into a 4-methylbenzyl thioether. The derivative has been used in the synthesis of a 22-residue peptide with a 62-atom cyclic disulfide. Amh(Meb) is stable to acidolysis but can be conveniently deprotected, with simultaneous disulfide formation, by treatment with diphenyl sulfoxide and trichloromethylsilane.
Nonenzymatic Dynamic Kinetic Resolution of in situ Generated Hemithioacetals: Access to 1,3-Disubstituted Phthalans
Nath, Utpal,Chowdhury, Deepan,Pan, Subhas Chandra
supporting information, p. 1628 - 1633 (2018/03/21)
The first nonenzymatic DKR reaction of hemithioacetals is developed. Hemithioacetals were formed in situ via thiol addition and subsequently underwent an intramolecular oxa-Michael reaction. The scope of the reaction was quite broad ranging from aliphatic to aromatic substituents and 1,3-disubstituted-1,3-dihyroisobenzofuran products were obtained in good yields with moderate diastereoselectivities and high enantioselectivities. (Figure presented.).
Phosphorus Pentasulfide Mediated Conversion of Primary Carbamates into Thiols
Maurya, Chandra Kant,Gupta, Pradeep Kumar
, p. 1649 - 1651 (2017/08/11)
In this paper, we report a method for the conversion of primary carbamates into thiols in the presence of phosphorus pentasulfide (P 2 S 5) in refluxing toluene. Presently, no method exists in the literature for conversion of carbamates into thiols and, to the best of our knowledge, it is the first report for this type of conversion. This method presents an indirect route for the conversion of alcohols into thiols via their carbamate derivatives that may be useful in the total synthesis of compounds containing a thiol functionality.