Diversity-Oriented Synthesis of Steviol Glycosides

With cheap and easily available mixtures of steviol glycosides as starting materials, a practical method for steviol acquisition has been developed, on the basis of which a facile, diversity-oriented, and economic protocol for the synthesis of structurally defined steviol glycosides was established....

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2018-10, Vol.83 (19), p.11480-11492
Main Authors: Qiao, Zhi, Liu, Hui, Sui, Jing-Jing, Liao, Jin-Xi, Tu, Yuan-Hong, Schmidt, Richard R, Sun, Jian-Song
Format: Article
Language:English
Subjects:
Carbohydrate Conformation
Chemistry Techniques, Synthetic
Diterpenes, Kaurane - chemistry
Glycosides - chemical synthesis
Glycosides - chemistry
Models, Molecular
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:With cheap and easily available mixtures of steviol glycosides as starting materials, a practical method for steviol acquisition has been developed, on the basis of which a facile, diversity-oriented, and economic protocol for the synthesis of structurally defined steviol glycosides was established. The novel approach is featured by the highly efficient glycosylation of sterically hindered and acid-sensitive steviol via orchestrated application of Yu glycosylation, Schmidt glycosylation, and PTC glycosylation. Hence, these high-intensity sweeteners and potential lead compounds for drug development are now readily accessible.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01274