Two novel N-glycoside 17, 18-unsaturated acid quinolin-3-ylmethyl ester josamycin derivatives. Issue 13 (28th March 2018)

• Record Type: Journal Article
• Authors: Zhao, Zhehui; Jin, Longlong; Wang, Apeng; Yang, Shuang; Lei, Pingsheng
• Is Part Of: Tetrahedron letters. Volume 59:Issue 13(2018)
• Page Start: 1208
• Page End: 1211
• Publication Date: 2018-03-28
• Subjects: Josamycin -- Nitro-glycoside -- Derivatives -- HWE reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.02.027
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Some novel N -glycoside josamycin derivatives were synthesized by coupling 4′-amino-desmycarosyl josamycin derivatives withl -mycarose. Highlights: Two novel N -glycoside josamycin derivatives, 9a and10a, were designed and synthesized. And two rearranged compounds9b and10b were also got. We reasoned the mechanism of formation of isomers4a and4b . We also confirmed the conformation of10a and10b, followed to reason the mechanism. Abstract: A facile procedure was developed to synthesize novel N -glycoside josamycin derivatives by coupling 4′-amino-desmycarosyl josamycin derivatives withl- mycarose. A novel N -glycoside josamycin derivative10a and a key intermediate9a were designed and synthesized. And two rearranged compounds9b and10b were also got.