1122091-19-3Relevant academic research and scientific papers
A flexible organocatalytic enantioselective synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its congeners
Kumaraswamy, Gullapalli,Sadaiah, Kadivendi
supporting information; experimental part, p. 262 - 271 (2012/01/14)
A unified enantioselective route is developed for the synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its synthetic congeners. A proline-catalyzed aminoxylation, cross-metathesis, Wittig reaction, and catalytic dihydroxylation are key steps
Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine
Shimada, Yasutaka,Usuda, Kazumasa,Okabe, Hirokazu,Suzuki, Tsuguru,Matsumoto, Kazutsugu
experimental part, p. 2802 - 2808 (2010/03/30)
The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates.
Preparation of optically active 1-O-alkyl-3-O-arylsulfonyl-sn-grycerol derivatives: Substrate engineering in enzyme-mediated enantioselective hydrolysis
Shimada, Yasutaka,Sato, Hiroshi,Mochizuki, Sachiyo,Matsumoto, Kazutsugu
scheme or table, p. 2981 - 2984 (2009/10/17)
Lipase PS catalyzes the enantioselective hydrolysis of various 2-acetyl compounds of the 1-O-alkyl-3-O-arylsulfonyl-sn-glycerol derivatives to afford the corresponding optically active compounds. Changing the structure of the 1-O-alkyl and 3-O-arylsulfonyl groups affects both the reactivity and enantioselectivity. Finally, the E value of the reaction for 2-acetyl-3-O-3,5-dimethylbenzenesulfonyl-1-O-4-methoxybenzyl-sn-glycerol is greater than 200. Georg Thieme Verlag Stuttgart.
