Convenient approaches to synthesis of furanoid sugar-aza-crown ethers from C-ribosyl azido aldehyde via a reductive amination/amidation

被引:11
作者
Hsieh, Yu-Chi [1 ]
Chir, Jiun-Ly [2 ]
Zou, Wei [3 ]
Wu, Hsiu-Han [1 ]
Wu, An-Tai [1 ]
机构
[1] Natl Changhua Univ Educ, Dept Chem, Changhua 50058, Taiwan
[2] Acad Sinica, Biotechnol Ctr So Taiwan, Sinshih Township 744, Tainan County, Taiwan
[3] Natl Res Council Canada, Inst Biol Sci, Ottawa, ON K1A 0R6, Canada
关键词
Furanoid; Sugar-aza-crown ether; Amination; Amidation; OLIGOSACCHARIDE MIMETICS; CYCLIC HOMOOLIGOMERS; AMINO-ACIDS;
D O I
10.1016/j.carres.2009.03.008
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
A short and highly efficient route to the alpha-anomer of a furanoid sugar-aza-crown ether was developed by a one-pot reductive amination of an alpha-anomer C-ribosyl azido aldehyde. In addition, the beta-anomer furanoid sugar-aza-crown ether was synthesized from a linear disaccharide precursor via amidation and then followed by microwave-assisted amide reduction. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1020 / 1023
页数:4
相关论文
共 13 条
[1]   POLYSACCHARIDE ANALOGS .3. 5-AMINO-2,6-ANHYDRO-5-DEOXY-D-GLYCERO-D-GULO-HEPTONIC ACID AND ITS POLYCONDENSATION TO OLIGOMERS [J].
FUCHS, EF ;
LEHMANN, J .
CARBOHYDRATE RESEARCH, 1976, 49 (JUL) :267-273
[2]   Cyclic homooligomers from sugar amino acids:: Synthesis, conformational analysis, and significance [J].
Locardi, E ;
Stöckle, M ;
Gruner, S ;
Kessler, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) :8189-8196
[3]   De Novo synthesis of sugar-aza-crown ethers via a domino Staudinger aza-Wittig reaction [J].
Ménand, M ;
Blais, JC ;
Valéry, JM ;
Xie, J .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (08) :3295-3298
[4]   Synthesis of orthogonally protected cyclic homooligomers from sugar amino acids [J].
Ménand, M ;
Blais, JC ;
Hamon, L ;
Valéry, JM ;
Xie, J .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11) :4423-4430
[5]  
MULLER G, 1995, J CHEM SOC CHEM COMM, P2425
[6]   Synthesis of a new carbohydrate mimetics: ''Carbopeptoid'' containing a C-1 carboxylate and C-2 amino group [J].
Suhara, Y ;
Hildreth, JEK ;
Ichikawa, Y .
TETRAHEDRON LETTERS, 1996, 37 (10) :1575-1578
[7]   Synthesis of sulfated beta-1,6-linked oligosaccharide mimetics: A novel potent inhibitor of HIV replication [J].
Suhara, Y ;
Ichikawa, M ;
Hildreth, JEK ;
Ichikawa, Y .
TETRAHEDRON LETTERS, 1996, 37 (15) :2549-2552
[8]   Solid phase synthesis and secondary structural studies of (1→5) amide-linked sialooligomers [J].
Szabo, L ;
Smith, BL ;
McReynolds, KD ;
Parrill, AL ;
Morris, ER ;
Gervay, J .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1074-1078
[9]   Parallel synthesis of cyclic sugar amino acid/amino acid hybrid molecules [J].
van Well, RM ;
Overkleeft, HS ;
Overhand, M ;
Carstenen, EV ;
van der Marel, GA ;
van Boom, JH .
TETRAHEDRON LETTERS, 2000, 41 (48) :9331-9335
[10]   Epimerization of 2′-carbonylalkyl-C-glycosides via enolation, β-elimination and intramolecular cycloaddition [J].
Wang, Z ;
Shao, HW ;
Lacroix, E ;
Wu, SH ;
Jennings, HJ ;
Zou, W .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21) :8097-8105