New and efficient synthesis of 5′-amino-5′-(S)-methyl-2′,5′-dideoxynucleosides

被引:16
作者
Jung, PMJ [1 ]
Beaudegnies, R [1 ]
De Mesmaeker, A [1 ]
Wendeborn, S [1 ]
机构
[1] Syngenta Crop Protect AG, CH-4002 Basel, Switzerland
关键词
5 '-amino-5 '-(S)-methyl-2 '; 5 '-dideoxynucleosides; tert-butylsulfinamide; nucleophilic addition;
D O I
10.1016/S0040-4039(02)02514-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short, efficient synthesis of 5'-amino-5'-(S)-methyl-2',5'-dideoxynucleosides 1 has been developed through the diastereoselective addition of methylmagnesium bromide or methyllithium to an intermediate tert-butylsulfinimide. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:293 / 297
页数:5
相关论文
共 26 条
[1]   An entry to unusual classes of nucleoside analogues [J].
Bar, NC ;
Patra, R ;
Achari, B ;
Mandal, SB .
TETRAHEDRON, 1997, 53 (13) :4727-4738
[2]   A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide [J].
Barrow, JC ;
Ngo, PL ;
Pellicore, JM ;
Selnick, HG ;
Nantermet, PG .
TETRAHEDRON LETTERS, 2001, 42 (11) :2051-2054
[3]   Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines [J].
Cogan, DA ;
Liu, GC ;
Ellman, J .
TETRAHEDRON, 1999, 55 (29) :8883-8904
[4]   CHAIN-EXTENSION OF CARBOHYDRATES .2. STEREOSPECIFIC ETHYNYLATION OF PROTECTED PYRANO-DIALDOSE AND FURANO-DIALDOSE [J].
CZERNECKI, S ;
VALERY, JM .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (01) :151-156
[5]   Concise asymmetric synthesis of α-amino acid derivatives from N-sulfinylimino esters [J].
Davis, FA ;
McCoull, W .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3396-3397
[6]  
DeMesmaeker A, 1997, SYNLETT, P1287
[7]   Amide backbone modifications for antisense oligonucleotides carrying potential intercalating substituents: Influence on the thermodynamic stability of the corresponding duplexes with RNA- and DNA-complements [J].
DeMesmaeker, A ;
Wendeborn, S ;
Jouanno, C ;
Fritsch, V ;
Wolf, RM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (14) :1869-1874
[8]  
DeMesmaeker A, 1997, BIOORG MED CHEM LETT, V7, P447, DOI 10.1016/S0960-894X(97)00037-1
[9]   REPLACEMENT OF THE PHOSPHODIESTER LINKAGE IN OLIGONUCLEOTIDES - COMPARISON OF 2 STRUCTURAL AMIDE ISOMERS [J].
DEMESMAEKER, A ;
LEBRETON, J ;
WALDNER, A ;
FRITSCH, V ;
WOLF, RM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (07) :873-878
[10]   Amide backbones with conformationally restricted furanose rings: Highly improved affinity of the modified oligonucleotides for their RNA complements [J].
DeMesmaeker, A ;
Lesueur, C ;
Bevierre, MO ;
Waldner, A ;
Fritsch, V ;
Wolf, RM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2790-2794