Efficient microwave assisted access to chiral O-(α-protected-aminoacyl)steroids

被引:32
作者
Katritzky, Alan R. [1 ]
Angrish, Parul [1 ]
机构
[1] Univ Florida, Dept Chem, Ctr Heterocycl Ctds, Gainesville, FL 32611 USA
关键词
N-(Z-alpha-aminoacyl)benzotriazole; O(alpha-protected-aminoacyl)steroid; O-acylation; chirality; microwave;
D O I
10.1016/j.steroids.2006.04.003
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
Chiral O-(alpha-protected-amino acyl)steroids 4a-f, 6a-b, 8 and 4a+4d and O-(alpha-protected-dipeptidoyl) steroids 12a,b are conveniently prepared under microwave irradiation in isolated yields of 65-96%, with complete chirality retention. The reaction utilized readily available N-(Z-alpha-aminoacyl)benzotriazoles 2a-f and Z-dipeptidoylbenzotriazole 11, with naturally occurring steroidal alcohols 3,5,7,9. (c) 2006 Elsevier Inc. All rights reserved.
引用
收藏
页码:660 / 669
页数:10
相关论文
共 55 条
[31]   Synthesis of β-dicarbonyl compounds using 1-acylbenzotriazoles as regioselective C-acylating reagents [J].
Katritzky, AR ;
Pastor, A .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12) :3679-3682
[32]   SYNTHESIS OF SOME STEROIDAL ESTERS OF ALPHA-AMINO-ACIDS [J].
LAPATSANIS, L ;
PROFILIS, C ;
CATSOULACOS, P .
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1980, 25 (03) :287-289
[33]   BENZYL ESTERS OF AMINO ACIDS [J].
MILLER, HK ;
WAELSCH, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (04) :1092-1093
[34]   PEPTIDYL AMINOSTEROIDS AS POTENTIAL NEW ANTIARRHYTHMIC AGENTS [J].
MOKOTOFF, M ;
ZHAO, M ;
MARSHALL, RJ ;
WINSLOW, E ;
WONG, LK ;
LIAO, QJ .
STEROIDS, 1990, 55 (09) :399-404
[35]   Organogelation of diacetylene cholesteryl esters having two urethane linkages and their photopolymerization in the gel state [J].
Nagasawa, J ;
Kudo, M ;
Hayashi, S ;
Tamaoki, N .
LANGMUIR, 2004, 20 (19) :7907-7916
[36]   N,N '-Carbonyldiimidazole, a new peptide forming Reagent [J].
Paul, Rolf ;
Anderson, George W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (17) :4596-4600
[37]   Ac2O-Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation [J].
Paul, S ;
Nanda, P ;
Gupta, R ;
Loupy, A .
TETRAHEDRON LETTERS, 2002, 43 (23) :4261-4265
[38]   The cholesterol membrane anchor of the hedgehog protein confers stable membrane association to lipid-modified proteins [J].
Peters, C ;
Wolf, A ;
Wagner, M ;
Kuhlmann, J ;
Waldmann, H .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (23) :8531-8536
[39]  
PROFILIS C, 1983, EUR J MED CHEM, V18, P567
[40]   1,1'-CARBONYLBIS(3-METHYLIMIDAZOLIUM) TRIFLATE - AN EFFICIENT REAGENT FOR AMINOACYLATIONS [J].
SAHA, AK ;
SCHULTZ, P ;
RAPOPORT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4856-4859