4073-59-0Relevant academic research and scientific papers
A convenient method for the preparation of functionalized N-acylsulfenamides from primary amides
Musiejuk, Mateusz,Witt, Dariusz
supporting information, p. 305 - 310 (2016/02/18)
We have developed a convenient method for the synthesis of functionalized N-acylsulfenamides under mild conditions and in moderate to good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives with nitrogen nucleophiles generated from primary amides or imides and sodium hydride. The developed method allows for the preparation of N-acylsulfenamides bearing additional hydroxyl, carboxyl, or amino functionalities.
DDQ-mediated synthesis of functionalized unsymmetrical disulfanes
Musiejuk, Mateusz,Klucznik, Tomasz,Rachon, Janusz,Witt, Dariusz
, p. 31347 - 31351 (2015/04/22)
We developed a simple and efficient method for the synthesis of functionalized unsymmetrical disulfanes under mild conditions in good yields. The designed method is based on the reaction of bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfane with thiols in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). The developed method allows the preparation of unsymmetrical disulfanes bearing additional hydroxy, carboxy, or amino functionalities.
TBAF promoted formation of symmetrical trisulfides
Lach, Slawomir,Witt, Dariusz
, p. 10 - 14 (2014/02/14)
We have developed a new method for the synthesis of functionalized symmetrical trisulfides based on (5,5-dimethyl-2-thioxo-1,3,2-dioxa-phosphorin- 2-yl)disulfanyl derivatives prepared from readily available 5,5-dimethyl-2-sul- fanyl-2-thioxo-1,3,2-dioxaph
Efficient synthesis of functionalized unsymmetrical dialkyl trisulfanes
Lach, Slawomir,Witt, Dariusz
supporting information, p. 1927 - 1930 (2013/09/24)
We have developed a convenient method for the synthesis of functionalized unsymmetrical dialkyl trisulfanes under mild conditions in very good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2- dioxaphosphorinan-2-yl)-di
An efficient and convenient synthesis of unsymmetrical disulfides from thioacetates
Lach, Slawomir,Demkowicz, Sebastian,Witt, Dariusz
supporting information, p. 7021 - 7023 (2013/12/04)
We have developed convenient methods for the synthesis of functionalized unsymmetrical dialkyl disulfides under mild conditions in very good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2- dioxaphosphorinan-2-yl)-disu
S-Alk(en)ylmercaptocysteine: Chemical synthesis, biological activities, and redox-related mechanism
Zhang, Guodong,Parkin, Kirk L.
, p. 1896 - 1903 (2013/08/25)
S-Alk(en)ylmercaptocysteine (CySSR, R = methyl, ethyl, propyl, 1-propenyl, and allyl), which are the putative metabolites of Allium thiosulfinates, were chemically synthesized. CySSR, but not the corresponding monosulfide species S-alk(en)yl cysteine (CyS
Cysteine and glutathione mixed-disulfide conjugates of thiosulfinates: Chemical synthesis and biological activities
Zhang, Guodong,Ll, Bln,Lee, Chen-Hsien,Parkin, Klrk L.
experimental part, p. 1564 - 1571 (2010/09/09)
The chemical syntheses of cysteine (CYS) and glutathione (GSH) mixed -disulfide conjugates (CySSR, GSSR, respectively) of mercapto residues representing most of the R groups of thiosulfinates (R = methyl, ethyl, propyl, and allyl) are described. Gram-scale conjugates were prepared as >98% pure preparations, with 80% reaction yield for each of the two seminal synthesis steps, with structures confirmed by 1H NMR and high-resolution MS analyses. These conjugates are derivatives of thiosulfinates that may be evolved in processed foods, in the digestive tract, and through in vivo metabolism. The prepared conjugates were found to be able to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7), indicating they have potential cancer preventive and anti-inflammatory activities. Among the prepared conjugates, the allyl conjugates of CYS and GSH, S-allylmercaptocysteine (CySSA) and S-allylmercaptoglutathione (GSSA), showed the most potent activity regarding QR induction and NO production inhibition. The conjugates with saturated R groups were also active and conferred biological activity as cystine and oxidized glutathione exhibited no effects in these cellular assays.
New derivatives of α-and β-dithiophosphates of 2-bromo-2-deoxy sugars
Borowiecka
, p. 793 - 798 (2007/10/03)
New derivatives of 2-bromo-2-deoxy hexopyranose, α-and β-glycosyl dithiophosphates 6-11, were synthesized by three methods: (A) by glycosylation of alkyl salts 1-3 of phosphorodithio acids with α-1,2-D-gluco and α-1-2-D-manno dibromides 4, 5; (B) by reaction of 4 or 5 with free phosphorodithio acids 12-14 activated by Lewis acid; (C) by addition of dithioacids 12-14 to 2-bromo-D-glucal 15.
REACTION OF BIS-- AND BIS--DISULFIDES WITH TRIALKYLSILYLCYANIDES. NEW ROUTE TO DIALKYLPHOSPHORO- AND DIALKYLTHIOPHOSPHORO THIOCYANIDATES AND O,O,O,O-TETRAALKYLPYROPHOSPHOROTRITHIOATES
Lopusinski, Andrzej,Luczak, Lech,Brzezinska, Ewa
, p. 101 - 108 (2007/10/02)
The reaction of organophosphorus disulfides with trialkylsilylcyanide has been investigated.It provided direct evidence for the intermediacy of thiocyanidate >P(X)SCN, X=O, S in this type of reaction.The disulfides studied involved phosphoryl, phosphonyl and/or phosphinyl disulfides.They have been shown to follow the common mechanism.The studied reaction of thiophosphoryl disulfides with trimethylsilylcyanide represents a new and highly efficient route to tetraalkylpyrophosphorotrithioates.
