145121-59-1Relevant academic research and scientific papers
The Regioselective Opening of 5-O-Benzyl-1,2:3,4-O-isopropylidene-D-psicofuranose With Organostannanes
Dillon, Michael P.,Maag, Hans,Muszinsky, Dawn M.
, p. 5469 - 5470 (2007/10/02)
The trimethylsilyl triflate mediated regioselective opening of 5-O-benzyl-1,2:3,4-O-isopropylidene-D-psicofuranose with organostannanes is presented.Hydrolysis of the initially formed 1-O-trimethylsilyl ether yields the products of S- and C-glycosidation with predominantly β-stereochemistry in good yields.The unusual addition of acetonitrile to the intermediate oxonium ion when the reaction is performed in this medium is also outlined.
Stereocontrolled synthesis of spirosuccinimide derivative of (+)-hydantocidin
Sano, Hiromi,Mio, Shigeru,Tsukaguchi, Naoto,Sugai, Soji
, p. 1387 - 1394 (2007/10/02)
Synthesis of the spirosuccinimide derivative of (+)-hydantocidin 2 is reported. The key step is a SnCl4-promoted C-glycosidation of the protected D-psicose 3 with allyltrimethylsilane in dichloromethane, which proceeded in good yield and high selectivity; however, C-glycosidation of 3 in acetonitrile afforded the spirooxazoline 6. Synthesis of 2 was achieved in 13% overall yield from 3.
