One-Pot Stereoselective Synthesis of 2,3,4-Unprotected β-N-Glycopyranosides from Glycals and Amines

被引：5

作者：

Gao, Jingyu ^{[1
]}

Li, Yi ^{[1
]}

Wang, Nengzhong ^{[1
]}

Li, Zhiyue ^{[1
]}

Huang, Nianyu ^{[1
]}

Yao, Hui ^{[1
]}

机构：

[1] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Key Lab Funct Yeast China Natl Light Ind, Yichang 443002, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 14期

基金：

湖北省教育厅重点项目; 中国国家自然科学基金;

关键词：

N-Glycosides; Tsuji-Trost amination; One-pot synthesis; Palladium catalysis; BETA-C-GLYCOSYLATION; N-GLYCOSYLATION; ARYLBORONIC ACIDS; O-GLYCOSYLATION; GLYCOSIDES; REARRANGEMENT; NUCLEOSIDES; AIR; AMPHIMEDOSIDES; PROGRESS;

D O I：

10.1002/adsc.202300211

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A one-pot synthesis of 2,3,4-unprotected & beta;-N-glycopyranosides from glycals and amines with exclusive & beta;-stereoselectivity under room temperature conditions is reported. This method was achieved via palladium-catalyzed Tsuji-Trost amination followed by dihydroxylation directly, tolerating anilines, heterocyclic aromatic amines, and N,O-dimethylhydroxylamine, especially the reaction of primary amines and glycals has not been reported before. Furthermore, the protocol was applied to modify clinical drugs (prazosin, imiquimod) and construct the analogue of the natural product amphimedoside A.

引用

页码：2350 / 2355

页数：6

共 50 条

[1] Regio and Stereoselective One-Pot Synthesis of 2-Deoxy-3-thio Pyranoses and Their O-Glycosides from Glycals
Bhardwaj, Monika
Mukherjee, Debaraj
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09): : 5676 - 5686
[2] One-pot synthesis of N-unprotected azacyclopentylidene complexes from their oxaanalogues
Haase, WC
Dötz, KH
TETRAHEDRON LETTERS, 1999, 40 (15) : 2919 - 2920
[3] A mild and easy one-pot procedure for the synthesis of 2-deoxysugars from glycals
Costantino, V
Imperatore, C
Fattorusso, E
Mangoni, A
TETRAHEDRON LETTERS, 2000, 41 (47) : 9177 - 9180
[4] One-Pot Synthesis of N-Glycooxazolines, N-Glycoaminooxazolines, and N-Glycothiazolines from Glycals
Reid, Erica M.
Vigneau, Edward S.
Gratia, Synthia S.
Marzabadi, Cecilia H.
De Castro, Michael
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (17) : 3295 - 3303
[5] A highly stereoselective one-pot asymmetric synthesis of homoallylic amines and amino acids from aldehydes
Loh, T.-P.
Ho, D. S.-C.
Xu, K.-C.
Sim, K.-Y.
Tetrahedron Letters, 38 (05):
[6] A highly stereoselective one-pot asymmetric synthesis of homoallylic amines and amino acids from aldehydes
Loh, TP
Ho, DSC
Xu, KC
Sim, KY
TETRAHEDRON LETTERS, 1997, 38 (05) : 865 - 868
[7] Stereoselective Synthesis of Ribofuranoid exo-Glycals by One-Pot Julia Olefination Using Ribofuranosyl Sulfones
Oka, Natsuhisa
Mori, Ayumi
Suzuki, Kanna
Ando, Kaori
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 657 - 673
[8] Selective One-Pot Cascade Synthesis of N-Substituted Highly Functionalized Pyrroles from Unprotected Sugars, Primary Amines, and Oxoacetonitriles
Mengxin, Xia
Lambu, Mallikharjuna Rao
Judeh, Zaher M. A.
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (18): : 12115 - 12131
[9] A tandem Heck-aza-Michael addition protocol for the one-pot synthesis of isoindolines from unprotected amines
Chen, Ke
Pullarkat, Sumod A.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (32) : 6600 - 6606
[10] Stereoselective one-pot synthesis of vinylsilanes from aromatic aldehydes
Kwan, ML
Yeung, CW
Breno, KL
Doxsee, KM
TETRAHEDRON LETTERS, 2001, 42 (08) : 1411 - 1413

← 1 2 3 4 5 →