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
[1]  
Bodanszky M., 1976, PEPTIDE SYNTHESIS
[2]  
CATSOULA.P, 1973, CANCER CHEMOTH REP 1, V57, P365
[3]   Electrostatic catalysis by ionic aggregates:: scope and limitations of Mg(ClO4)2 as acylation catalyst [J].
Chakraborti, AK ;
Sharma, L ;
Gulhane, R ;
Shivani .
TETRAHEDRON, 2003, 59 (39) :7661-7668
[4]  
CIPERA JD, 1955, CHEM INT, V1, P16
[5]   ESTERIFICATION OF N-PROTECTED ALPHA-AMINO-ACIDS WITH ALCOHOL/CARBODIIMIDE/4-(DIMETHYLAMINO)-PYRIDINE - RACEMIZATION OF ASPARTIC AND GLUTAMIC-ACID DERIVATIVES [J].
DHAON, MK ;
OLSEN, RK ;
RAMASAMY, K .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1962-1965
[6]   IMPROVED SYNTHESIS OF AMINO ACID BENZYL ESTERS [J].
ERLANGER, BF ;
HALL, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (22) :5781-5782
[7]  
Gao X, 1995, GENE THER, V2, P710
[8]   CARBOXY-TERMINUS COUPLING USING 1,1'-CARBONYLBIS(3-METHYLIMIDAZOLIUM TRIFLATE) (CBMIT) IN THE PRESENCE OF CU(II) SALTS [J].
GIBSON, FS ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) :2615-2617
[9]  
GOOBEN LJ, 2004, SYNLETT, V2, P263
[10]  
GROSS M, 1979, PEPTIDES