64826-51-3

Upstream product

• 180253-98-9 Phenylsulfanylamino-acetic acid ethyl ester 
• 3696-28-4 2,2'-dipyridyl disulfide bis-N-oxide 
• 1121-31-9 2-mercaptopyridine N-oxide 
• 108-98-5 thiophenol 
• 931-59-9 benzenesulfenyl chloride 
• 14933-91-6 N-phenyl-benzenesulphenamide 
• 104047-14-5 4-Nitro-benzoic acid 2-thioxo-2H-pyridin-1-yl ester 
• 114050-46-3 N-(4-methoxybenzoyloxy)-pyridine-2(1H)-thione 
• 22574-12-5 Phenylcarbonyloxy(pyridine-2-thione) 
• 6667-19-2 benzenenesulfenyl dimethylamine 
• 91233-19-1 1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione 
• 114050-31-6 3-Phenyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 105398-69-4 Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester 
• 180253-99-0 (Methyl-phenylsulfanyl-amino)-acetic acid ethyl ester 

Downstream Products

• 1121-30-8 1-hydroxy-2(1H)-pyridinethione 
• 20126-55-0 2-propyl-1-phenyldisulfane 
• 882-33-7 diphenyldisulfane 

Relevant academic research and scientific papers

New reactions of the thiocarbonyl function. The synthesis of hindered peptides

The well-known radical chemistry of the thiocarbonyl function has been expanded to include the concerted reaction between an O-acyl derivative of N-hydroxypyridine-2(1H)-thione (a Barton PTOC ester) and a sulfenamide. The atom-economical process spawned a carboxamide and an unsymmetrical disulfide of synthetic and biological value. The reaction was successfully applied to the synthesis of sterically encumbered, urethane-protected dipeptides. The oxidation-reduction technology pertaining to the disulfide-phosphine combination facilitated the generation of transient Barton PTOC esters. In conjunction with the appropriate benzenesulfenamide, the Barton PTOC ester of benzoyl-L-leucine was shown to preserve optical integrity according to the sensitive Young test, albeit at low temperature. However, the thermodynamic forces at play are powerful and, as a result, the yields were not compromised. In all but the sterically demanding instances, the parent free amine almost matched the reaction time, yield, and enantiomeric excess of the corresponding benzenesulfenamide in its reaction with a Barton PTOC ester.

N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part II. Applications in peptide synthesis

The N-hydroxypyridine-2(1H)-thione derivatives of two urethane-protected α-amino acids readily reacted with the α-amino acid esters or the corresponding benzenesulfenamides to give simple dipeptides in reasonable yields. The benzenesulfenamides are the re

N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part I. The synthesis of carboxamides

The reaction between an acyl derivative of N-hydroxypyridine-2(1H)- thione (a Barton PTOC ester) and either an amine (primary or secondary), or the corresponding sulfenamide, led to the formation of a carboxamide in a clean transformation requiring minimal work-up and purification. The reaction with a sulfenamide is particularly useful since the only by-product, an unsymmetrical disulfide, is of both synthetic and biological value. In sterically demanding cases, Barton PTOC esters were more reactive towards benzenesulfenamides than to the corresponding free amines.

Synthesis of Disulfides via Sulfenylation of Alkyl and Aryldithiopyridine N-Oxides

Alkyl and aryldithiopyridine N-oxides were prepared by reaction of 2,2'-dithiopyridine-1,1'-dioxide with various thiols in high yields.Some of the mixed disulfide products could in turn be used to sulfenylate efficiently other thiols.Therefore, practical and efficient synthetic methods for both symmetrical and unsymmetrical disulfides were developed.

Unsymmetrical disulfides as antimicrobial agents

Novel unsymmetrical disulfides of pyridine-1-oxide and acid addition salts thereof, having particular utility as antimicrobial agents per se and in skin cleansing detergent compositions, shampoos, hair dressings, disinfectants, preservatives and the like.