Facile synthesis of flavonoid 7-O-glycosides

被引：89
作者：
Li, M
Han, XW
Yu, B
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalyst, Dalian 116023, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 17期
关键词：
D O I：
10.1021/jo034553e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly regioselective removal of the 7-O-acylgroups of the peracyated flavones, isoflavones, and flavonolsyl(PhSH, imidazole, NMP) followed by effective glycosylation with glycosyl trifluoroacetimidates (BF3.Et2O) and cautious deprotection of the acyl groups under basic conditions afforded the desired 7-O-flavonoid glycosides in satisfactory yields.
引用
收藏
页码：6842 / 6845
页数：4
相关论文
共 50 条
[1]  
Alluis B, 2001, HELV CHIM ACTA, V84, P1133, DOI 10.1002/1522-2675(20010516)84:5<1133::AID-HLCA1133>3.0.CO
[2]  
2-Z
[3]  
Alluis B, 1999, HELV CHIM ACTA, V82, P2201, DOI 10.1002/(SICI)1522-2675(19991215)82:12<2201::AID-HLCA2201>3.0.CO
[4]  
2-4
[5]  
[Anonymous], 1999, HDB NATURAL FLAVONOI
[6]   Kinetics and mechanism of the base-catalyzed oxygenation of flavonol in DMSO-H2O solution [J].
Balogh-Hergovich, É ;
Speier, G .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7974-7978
[7]  
BRUNKE RA, 1996, Patent No. 4432947
[8]   Influence of hydrogen bonding in the activation of nucleophiles:: PhSH-(catalytic) KF in N-methyl-2-pyrrolidone as an efficient protocol for selective cleavage of alkyl/aryl esters and aryl alkyl ethers under nonhydrolytic and neutral conditions [J].
Chakraborti, AK ;
Sharma, L ;
Nayak, MK .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2541-2547
[9]   Selective deprotection of aryl acetates, benzoates, pivalates, and tosylates under nonhydrolytic and virtually neutral conditions [J].
Chakraborti, AK ;
Nayak, MK ;
Sharma, L .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :8027-8030
[10]   GLYCOSIDES .1. NEW SYNTHESIS OF 1,2-TRANS O-ARYL GLYCOSIDES, VIA TRIBUTYLTIN PHENOXIDES [J].
CLERICI, F ;
GELMI, ML ;
MOTTADELLI, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (08) :985-988
12345