First total syntheses of two natural glycosides. (January 2021)

• Record Type: Journal Article
• Authors: Dong, Hongbo; Du, Weihong; Yao, Zhongquan; Wu, Min; Luo, Hongbing; He, Yujiao; Cao, Shenghua
• Is Part Of: Carbohydrate research. Volume 499(2021)
• Publication Date: 2021-01
• Subjects: Total synthesis -- Glycosides -- Isosyringinoside -- 3-(O-β-d-glucopyranosyl)-α-(O-β-d-glucopyranosyl)-4-hydroxy phenylethanol; 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.2020.108200
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Isosyringinoside (1 ) and 3-( O - β -d -glucopyranosyl)-α-( O - β -d -glucopyranosyl)-4-hydroxy phenylethanol (2 ), the natural bioactive compounds contained unique structures, were first totally synthesized using easily available materials in short convenient routes with overall yields of 20.2% and 27.0%, respectively. An efficient total synthesis of 1 was developed in six steps, which contained two key steps of highly regioselective glycosylation without any selective protection steps. The seven-step synthesis of 2 involved two steps of regioselective glycosylations using BF3 –O(C2 H5 )2 and TMSOTf as catalysts, respectively. Graphical abstract: Two natural bioactive glycosides, Isosyringinoside (1 ) and 3-( O - β -d -glucopyranosyl)-α-( O - β -d -glucopyranosyl)-4-hydroxy phenylethanol (2 ), were first totally synthesized via 6–7 steps with overall yields of 20.2% and 27.0%, respectively. Image 1 Highlights: Isosyringinoside and 3-( O - β -d -glucopyranosyl)-α-( O - β -d -glucopyranosyl)-4-hydroxy phenylethanol were totally synthesized. The reported syntheses routes were short and convenient, using commercially available starting materials. This methodology was efficient and scalable and could be adopted for syntheses of other natural bioactive glycosides.