914910-71-7Relevant academic research and scientific papers
Preparation and odour properties of (S)-3-mercapto-1-heptyl acetate
Liang, Sen,Sun, Baoguo,Yang, Shaoxiang,Liu, Yongguo,Tian, Hongyu,Liu, Yuping,Chen, Haitao
, p. 343 - 346 (2014/07/08)
Synthesis of (S )-3-mercapto-1-heptyl acetate was achieved in four steps. Sharpless asymmetric epoxidation of (E )-2-heptenol yielded (2R,3R )-2,3-epoxy-1-heptanol, which was treated with thiourea in the presence of Ti(OPri)4 to give (2S,3S )-2,3-epithio- 1-heptanol, reduction of which followed by acetylation afforded (S )-3-mercapto-1-heptyl acetate in 91% ee. The optically active product possessed a tropical fruit aroma reminiscent of mango and passion fruit, with berry, ester-like, sweet, and pepper-like aspects.
