Synthesis of bidesmosidic lupane saponins – comparison of batch and continuous-flow methodologies. (22nd May 2018)

• Record Type: Journal Article
• Authors: Korda, Anna; Pakulski, Zbigniew; Cmoch, Piotr; Gwardiak, Katarzyna; Karczewski, Romuald
• Is Part Of: Carbohydrate research. Volume 461(2018)
• Page Start: 32
• Page End: 37
• Publication Date: 2018-05-22
• Subjects: Lupane bidesmosides -- Glycosylation -- Betulin -- The Wagner-Meerwein rearrangement -- Microreactors; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2018.03.006
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Synthesis of lupane bidesmosides was optimized. The title compounds were obtained by glycosylation of 3- O - or 28- O -substituted betulin monodesmosides with Schmidt donors catalyzed by TMSOTf. Classical batch procedure and microreactor technique were used and compared in the above synthesis. Experimental results clearly showed that both methods are comparable, although any particular outcome strongly depends on the structure of the reagents. Undesired allobetulin derivatives formed by the Wagner-Meerwein rearrangement were usually isolated in minute amounts. In the case of batch reaction, shorter reaction time significantly decreased formation of side-products. Graphical abstract: Highlights: Glycosylation of monodesmosidic saponins was described. Lupane-type bidesmosidic saponins were prepared. Classical batch procedure and microreactor technique were compared in the above synthesis. Influence of reaction conditions on the Wagner-Meerwein rearrangement was described. Applications of microflow technique to the synthesis of lupane bidesmosides was described.