Stereoselective and Regioselective Preparation of C‐Pentopyranosides and Formal Synthesis of Omarigliptin. Issue 34 (7th November 2016)

• Record Type: Journal Article
• Authors: Liu, Tongchao; Hou, Jian; Xie, Wuchen; Li, You; Ren, Huanming; Liang, Jianpeng; Xiong, Bing; Chen, Guohua; Cheng, Maosheng; Zhao, Dongmei; Shen, Jingkang; Chen, Yue‐Lei
• Is Part Of: European journal of inorganic chemistry. Issue 34(2016)
• Page Start: 5624
• Page End: 5628
• Publication Date: 2016-11-07
• Subjects: Asymmetric synthesis -- C‐glycosides -- Drug design -- Epoxides -- Glycosylation; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejoc.201601074
• Languages: English
• ISSNs: 1434-1948

Abstract

Abstract : A readily available intermediate obtained fromd ‐arabinose was identified as a versatile starting material for the stereoselective synthesis of C ‐pentopyranosides in one pot. For two of the C ‐pentopyranosides, subsequent epoxide ring formation and a regioselective opening process was proven to be a robust approach to 3‐deoxy C ‐pentopyranosides in two to four steps. A key intermediate used in the preparation of omarigliptin was obtained in four steps. Most of the conversions were high‐yielding and proceeded with high selectivities on a multigram scale. Abstract : Through a stereoselective C ‐glycosylation reaction and a versatile epoxide approach and starting from readily available carbohydrate chiral pool lactone8, some valuable C ‐pentopyranosides and 3‐deoxy C ‐pentopyranosides, including compound7 as a key intermediate in the preparation of omarigliptin, are prepared efficiently. TBS = tert ‐butyldimethylsilyl; Boc = tert ‐butoxycarbonyl.