FeCl3-catalyzed α-glycosidation of glycosamine pentaacetates

被引：30
作者：
Wei, Guohua [1 ]
Lv, Xun [1 ,2 ]
Du, Yuguo [1 ,2 ]
机构：
[1] Chinese Acad Sci, Ecoenvironm Sci Res Ctr, State Key Lab Environm Chem & Ecotoxicol, Beijing 100085, Peoples R China
[2] Chinese Acad Sci, Grad Univ, Coll Chem & Chem Engn, Beijing 100049, Peoples R China
来源：
CARBOHYDRATE RESEARCH | 2008年 / 343卷 / 18期
关键词：
Glycopeptide; Mucin; Ferric chloride; alpha-Glycoside; T-N-Antigen;
D O I：
10.1016/j.carres.2008.09.003
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
An efficient method for the large-scale preparation of alpha-N-acetylglycosaminides, such as fluorogenic T-N-antigen probes and an alpha-GaINAc-Ser derivative, has been achieved using FeCl3-catalyzed one-step condensation between commercially available D-glycosamine pentaacetates and fluorogenic acceptors (or serine acceptor) in refluxing 1,2-dichloroethane. Experimental simplicity, high alpha-stereoselectivity, low cost, satisfactory yield, and the environmentally benign nature are major advantages of our approach. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3096 / 3099
页数：4
相关论文
共 32 条
[11]   Stereo selectivity investigation on glycosylation of oxazolidinone protected 2-amino-2-deoxy-D-glucose donors based on pre-activation protocol [J].
Geng, Yiqun ;
Zhang, Li-He ;
Ye, Xin-Shan .
TETRAHEDRON, 2008, 64 (22) :4949-4958
[12]   Pre-activation protocol leading to highly stereoselectivity-controllable glycosylations of oxazolidinone protected glucosamines [J].
Geng, Yiqun ;
Zhang, Li-He ;
Ye, Xin-Shan .
CHEMICAL COMMUNICATIONS, 2008, (05) :597-599
[13]  
Hodosi G, 1996, SYNLETT, P159
[14]   FERRIC-CHLORIDE, AN ANOMERIZATION CATALYST FOR THE PREPARATION OF ALKYL ALPHA-GLYCOPYRANOSIDES [J].
IKEMOTO, N ;
KIM, OK ;
LO, LC ;
SATYANARAYANA, V ;
CHANG, M ;
NAKANISHI, K .
TETRAHEDRON LETTERS, 1992, 33 (30) :4295-4298
[15]   Di-tert-butylsilylene-directed α-selective synthesis of 4-methylumbelliferyl T-antigen [J].
Imamura, A ;
Ando, H ;
Ishida, H ;
Kiso, M .
ORGANIC LETTERS, 2005, 7 (20) :4415-4418
[16]   Iodine and its interhalogen compounds:: versatile reagent in carbohydrate chemistry.: XX.: Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides [J].
Kaerkkaeinen, Tiina S. ;
Kartha, K. P. Ravindranathan ;
MacMillan, Derek ;
Field, Robert A. .
CARBOHYDRATE RESEARCH, 2008, 343 (10-11) :1830-1834
[17]   Extended applications and potential limitations of ring-fused 2,3-oxazolidinone thioglycosides in glycoconjugate synthesis [J].
Kerns, RJ ;
Zha, CX ;
Benakli, K ;
Liang, YZ .
TETRAHEDRON LETTERS, 2003, 44 (44) :8069-8072
[18]   PROTECTED GLYCOSIDES AND DISACCHARIDES OF 2-AMINO-2-DEOXY-D-GLUCOPYRANOSE BY FERRIC CHLORIDE-CATALYZED COUPLING [J].
KISO, M ;
ANDERSON, L .
CARBOHYDRATE RESEARCH, 1985, 136 (FEB) :309-323
[19]   Synthetic and immunological studies on clustered modes of mucin-related Tn and TF O-linked antigens: The preparation of a glycopeptide-based vaccine for clinical trials against prostate cancer [J].
Kuduk, SD ;
Schwarz, JB ;
Chen, XT ;
Glunz, PW ;
Sames, D ;
Ragupathi, G ;
Livingston, PO ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (48) :12474-12485
[20]   AZIDONITRATION OF TRI-O-ACETYL-D-GALACTAL [J].
LEMIEUX, RU ;
RATCLIFFE, RM .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (10) :1244-1251
1234