The first total synthesis of rebaudioside R

被引：6

作者：

Wen, Guo-En ^{[1
]}

Qiao, Zhi ^{[1
]}

Liu, Hui ^{[1
]}

Zeng, Zhiyong ^{[1
]}

Tu, Yuan-Hong ^{[1
]}

Xia, Jian-Hui ^{[1
]}

Zhang, Qing-Ju ^{[1
]}

Sun, Jian-Song ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, 99 Ziyang Ave, Nanchang 330022, Jiangxi, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 01期

基金：

中国国家自然科学基金;

关键词：

STEVIA-REBAUDIANA BERTONI; DITERPENE GLYCOSIDES; GLYCOSYLATION; STEVIOSIDE; OLIGOSACCHARIDES; ALKYNYLBENZOATES;

D O I：

10.1039/c9ob02422k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

With easily available monosaccharides and steviol as starting materials, the first total synthesis of rebaudioside R with a xylosyl core in the C13-OH linked sugar chain was accomplished via two distinct approaches. The first approach features the stepwise installation of branch-sugar residues via an order of C2-OH first and then C3-OH of the xylosyl core, laying a firm foundation for the synthesis of analogues with different branch sugars, while the second route features the introduction of the C13 trisaccharide sugar chain via a convergent strategy, securing the overall synthetic efficiency. Through the synthetic study, the effect of protecting groups (PGs) at the vicinal hydroxy group on the reactivity of OH acceptors was illustrated.

引用

页码：108 / 126

页数：19

共 50 条

[31] The First Total Synthesis of (±)-Sinaiticin
1600, Higher Education Press (21):
[32] First Total Synthesis of (±)-Rhodoconferimide
Pandhade, Kailas R.
Argade, Narshinha P.
SYNTHESIS-STUTTGART, 2018, 50 (03): : 658 - 662
[33] The first total synthesis of (±)-saudin
Winkler, JD
Doherty, EM
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (32) : 7425 - 7426
[34] The first total synthesis of ligudentatin A
Zhang, Chen Xi
Bi, Fu Qiang
Li, Yu Lin
CHINESE CHEMICAL LETTERS, 2008, 19 (07) : 805 - 806
[35] First total synthesis of (+)-chrysanthemol
Chen, YG
Xiong, ZM
Zhou, G
Yang, J
Li, YL
CHEMISTRY LETTERS, 1997, (12) : 1289 - 1290
[36] First Total Synthesis of (±)-Aiphanol
Xiao Long WANG
Chinese Chemical Letters, 2004, (09) : 1036 - 1038
[37] First Total Synthesis of Varioxiranol A
Lasikova, Angelika
Dohanosova, Jana
Stiblarikova, Maria
Parak, Martin
Moncol, Jan
Gracza, Tibor
MOLECULES, 2019, 24 (05)
[38] First total synthesis of mariamide A
Xia, Yamu
Chen, Chenglong
Li, Mengying
Zhou, Weizeng
Sun, Shuyu
Chu, Shanpeng
Wang, Hui
JOURNAL OF CHEMICAL RESEARCH, 2020, 44 (1-2) : 114 - 120
[39] First total synthesis of tripdiolide
Zhou, Bing
Tang, Huanyu
Feng, Huijin
Li, Yuanchao
TETRAHEDRON, 2011, 67 (05) : 904 - 909
[40] First Total Synthesis of (+)-Caparratriene
Li, J.
Liu, Z.
Lan, J.
Li, Y.
Chemistry Letters, (03):

← 1 2 3 4 5 →