Synthesis of Deoxy Pyranosides Via Fe(III) Catalyzed Regioselective Thiocarbonylation of Partially Protected Carbohydrates

被引：1

作者：

Zhao, Jie ^{[1
]}

Zhang, Xiaorui ^{[1
]}

Yang, Qichang ^{[1
]}

Wang, Haifeng ^{[1
,2
]}

Gu, Shuang-Xi ^{[1
,2
]}

Yan, Qiongjiao ^{[1
]}

Lv, Jian ^{[1
]}

Chen, Fen-Er ^{[1
,3
,4
]}

机构：

[1] Wuhan Inst Technol, Pharmaceut Res Inst, Wuhan 430205, Peoples R China

[2] Wuhan Inst Technol, Sch Chem Engn & Pharm, Wuhan 430205, Peoples R China

[3] Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Dept Chem, Shanghai 200433, Peoples R China

[4] Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 33期

基金：

中国国家自然科学基金;

关键词：

Deoxysugars; Selective thiocarbonylation; FeCl3; catalysis; Deoxygenation; Green; SELECTIVE DEOXYGENATION; RADICAL DEOXYGENATION; INVENTION; SUGARS; CIS;

D O I：

10.1002/ejoc.202400512

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rapid and efficient synthesis of targeted deoxygenated glycosides is highly desired. Herein, we disclose a two-step procedure for the synthesis of deoxysugars from partially protected pyranosides via site-selective thiocarbonylation followed by tin-free Barton-McCombie deoxygenation. The selectivity can be smoothly achieved through anhydrous FeCl3 as the catalyst assisted by low-priced benzoyltrifluoroacetonate (Hbtfa) ligand in the presence of K2CO3 as base. Further deoxygenation can be carried out using greener silicon reagent, avoiding highly toxic organotin reagents in traditional procedures. Conspicuous features of this method include mild conditions, easy operation, high selectivity and non or low toxic reagents, making it a more attractive strategy.

引用

页数：5

共 37 条

[1] THE INVENTION OF RADICAL REACTIONS .21. SIMPLE METHODS FOR THE RADICAL DEOXYGENATION OF PRIMARY ALCOHOLS [J].

BARTON, DHR ;

BLUNDELL, P ;

DORCHAK, J ;

JANG, DO ;

JASZBERENYI, JC .

TETRAHEDRON, 1991, 47 (43) :8969-8984

[2] THE INVENTION OF RADICAL REACTIONS .24. RELATIVE RATES OF ACYLATION AND RADICAL DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

DORCHAK, J ;

JASZBERENYI, JC .

TETRAHEDRON, 1992, 48 (36) :7435-7446

[3] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[4] FeCl3 mediated arylidenation of carbohydrates [J].

Basu, Nabamita ;

Maity, Sajal K. ;

Roy, Soumik ;

Singha, Shuvendu ;

Ghosh, Rina .

CARBOHYDRATE RESEARCH, 2011, 346 (05) :534-539

[5] Methods for 2-Deoxyglycoside Synthesis [J].

Bennett, Clay S. ;

Galan, M. Carmen .

CHEMICAL REVIEWS, 2018, 118 (17) :7931-7985

[6] Iron(III) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides [J].

Bourdreux, Yann ;

Lemetais, Aurelie ;

Urban, Dominique ;

Beau, Jean-Marie .

CHEMICAL COMMUNICATIONS, 2011, 47 (07) :2146-2148

[7] A Unified Strategy to Access 2-and 4-Deoxygenated Sugars Enabled by Manganese-Promoted 1,2-Radical Migration [J].

Carder, Hayden M. ;

Suh, Carolyn E. ;

Wendlandt, Alison E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (34) :13798-13805

[8] Synthesis of chemical tools to label the mycomembrane of corynebacteria using modified iron(iii) chloride-mediated protection of trehalose [J].

Carlier, Mathieu ;

Lesur, Emilie ;

Baron, Aurelie ;

Lemetais, Aurelie ;

Guitot, Karine ;

Roupnel, Loic ;

Dietrich, Christiane ;

Doisneau, Gilles ;

Urban, Dominique ;

Bayan, Nicolas ;

Beau, Jean-Marie ;

Guianvarc'h, Dominique ;

Vauzeilles, Boris ;

Bourdreux, Yann .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (09) :1974-1981

[9]

Chatgilialoglu C, 1999, CHEM-EUR J, V5, P2866, DOI 10.1002/(SICI)1521-3765(19991001)5:10<2866::AID-CHEM2866>3.3.CO

[10]

2-Y

← 1 2 3 4 →