Organic disulfides and related substances. 32. Preparation and decomposition of .beta.-substituted ethyl acetyl disulfides

Abstract

Organic Disulfides and Related Substances. 32 corresponding carboxamide. This was unsuccessful; the only product, isolated in low yield, was 17: mp 130-131°; mass spectrum (70 eV) m/e (rel intensity) 273 (100), 159 (71), 114 (15), 81 (25).

Synthesis and Antibacterial Activity of Bis[2-amino-4-phenyl-5-thiazolyl] Disulfides

“…1). Literature reveals the availability of a variety of techniques for preparing both symmetric and unsymmertric disulfides, many of which are based upon the reaction of a thiol with a sulfenylating agent such as sulfenyl halides, 18) sulfenamides, 19) sulfinimides, 20) sulfenylhydrazides 21) and disulfides. 22) In the present case, sulfur monochloride in glacial acetic acid was proved to be excellent to synthesize the disulfide linkage as carbon of thiazole ring is very susceptible to S 2 Cl 2 thus avoiding the formation of the thiols first ( Table 2).…”

Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate

“…Disulfanyl acetates 2a , 2b 2c , 2d , 2e , 2f , and 2g , were all synthesized by reaction of the corresponding thiosulfonate (1 equiv) with potassium thioacetate (1.3 equiv) in DCM at rt for a few hours for aliphatic cases, and −40 °C for aromatic variants, the method modeled on a recent literature procedure . Here, the thiotosylate was always used as the limiting reagent and checked for total consumption (by TLC).…”

A highly efficient construction of GM1 epitope tetrasaccharide and its conjugation with KLH

“…Since maleimide-activated KLH is commercially available, we tried to introduce thiol function into the glycan part. 6-(Tert-butyldithio)hexanol (16) was prepared from 6-mercaptohexanol by a treatment with methoxycarbonylsulfenyl chloride [12] to give an asymmetrical disulfide 15 in 95%, which was transformed into the desired spacer part 16 by a treatment with 2-methyl-2-propanthiol in 99% yield (Scheme 3). The coupling of the glycosyl imidate 13 and the alcohol 16 was accomplished by a treatment with trimethylsilyl trifluoromethanesulfonate to give 17 in 87% yield.…”