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

[41] First total synthesis of quiquesetinerviusin A
Xia, Yamu
Mo, Zhen
Sun, Lin
Zou, Lijia
Zhang, Wen
Zhang, Jiahong
Wang, Lihong
JOURNAL OF CHEMICAL RESEARCH, 2017, (05) : 296 - 300
[42] First total synthesis of (±)-longianone
Steel, PG
CHEMICAL COMMUNICATIONS, 1999, (22) : 2257 - 2258
[43] FIRST TOTAL SYNTHESIS OF (-)-DEHYDROCARISSONE
LIU, LJ
XIONG, ZM
NAN, FJ
LI, TS
LI, YL
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1995, 104 (02): : 73 - 76
[44] First total synthesis of paecilodepsipeptide A
Yang, Ming Jun
Wu, Jing
Yang, Zhong Duo
Zhang, Ying Mei
CHINESE CHEMICAL LETTERS, 2009, 20 (05) : 527 - 530
[45] The first total synthesis of (±)-lagopodin A
Srikrishna, A
Lakshmi, BV
Ravikumar, PC
TETRAHEDRON LETTERS, 2006, 47 (08) : 1277 - 1281
[46] First total synthesis of (+)-Carainterol A
Ma, Kaiqing
Zhang, Chunbo
Liu, Mingming
Chu, Yong
Zhou, Lu
Hu, Changqi
Ye, Deyong
TETRAHEDRON LETTERS, 2010, 51 (14) : 1870 - 1872
[47] First total synthesis of paecilodepsipeptide A
Ming Jun Yang~(a
ChineseChemicalLetters, 2009, 20 (05) : 527 - 530
[48] First total synthesis of (±)-trolline
Qiu Qin He
ChineseChemicalLetters, 2007, (06) : 651 - 652
[49] The first total synthesis of (-)-tamandarin A
Liang, B
Portonovo, P
Vera, MD
Xiao, D
Joullié, MM
ORGANIC LETTERS, 1999, 1 (08) : 1319 - 1322
[50] The First Total Synthesis of Gravicycle
Ueda, Katsuaki
Sato, Itaru
Hirama, Masahiro
CHEMISTRY LETTERS, 2012, 41 (01) : 87 - 89

← 1 2 3 4 5 →