173739-06-5Relevant academic research and scientific papers
Synthesis of Bisdesmosidic Oleanolic Acid Saponins via a Glycosylation-Deprotection Sequence under Continuous Microfluidic/Batch Conditions
Konishi, Naruki,Shirahata, Tatsuya,Yokoyama, Masaki,Katsumi, Tatsuya,Ito, Yoshikazu,Hirata, Nozomu,Nishino, Takashi,Makino, Kazuishi,Sato, Noriko,Nagai, Takayuki,Kiyohara, Hiroaki,Yamada, Haruki,Kaji, Eisuke,Kobayashi, Yoshinori
, p. 6703 - 6719 (2017)
We report the first synthesis of a series of bisdesmosidic oleanolic acid saponins using microflow reactor Comet X-01 via a continuous flow glycosylation-batch deprotection sequence. The main results of this study can be summarized as follows: (1) The microfluidic glycosylation of oleanolic acid at C-28 was achieved in quantitative yield and was applied to the synthesis of six C-28-monoglycosidic saponins. (2) The microfluidic glycosylation of oleanolic acid at C-3 was achieved in good yield without orthoester byproduct formation and was applied to the synthesis of three bisdesmosidic saponins. (3) The continuous synthesis of saponins via a microfluidic glycosylation-batch deprotection sequence was achieved in four steps involving two purifications. Thus, the continuous microfluidic glycosylation-deprotection process is expected to be suitable for the preparation of a library of bisdesmosidic oleanolic acid saponins for in vivo pharmacological studies.
Facile synthesis of oleanolic acid monoglycosides and diglycosides
Sha, Yu,Yan, Mao-Cai,Liu, Jiao,Liu, Yang,Cheng, Mao-Sheng
, p. 1472 - 1486 (2008/12/21)
Oleanolic acid and its glycosides are important natural products, possessing various attractive biological activities such as antitumor, antivirus and anti-inflammatory properties. In the present work, fifteen oleanolic acid saponins bearing various sacch
