CONFORMATIONALLY RESTRICTED SPIN LABELED NUCLEOTIDES - A MODEL STUDY OF THE SYNTHESIS AND PROPERTIES OF THE 2',3'-O-SPIRO KETAL OF URIDINE AND 4-OXO-2,2,6,6-TETRAMETHYL-1-PIPERIDYLOXY

被引：7

作者：

ALESSI, DR

CORRIE, JET

FEENEY, J

TRAYER, IP

TRENTHAM, DR

机构：

[1] NATL INST MED RES,MILL HILL,LONDON NW7 1AA,ENGLAND

[2] UNIV BIRMINGHAM,SCH BIOCHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 09期

关键词：

D O I：

10.1039/p19910002243

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 2',3'-O-(1-oxy-2,2,6,6-tetramethyl-4-piperidylidene)uridine 13 is described in a model study directed at the corresponding spin labelled spiro ketal derivative of ATP (adenosine triphosphate) 1 and of other nucleotides. The synthesis proceeds via acid-catalysed addition of 5'-O-benzoyluridien to 1-acetoxy-4-methoxy-2,2,6,6-tetramethyl-1,2,5,6-tetrahydropyridine 9. The spiro ketal 11 from this reaction exists as two slowly interconverting conformers at room temperature. Prolonged alkaline hydrolysis and concomitant aerial oxidation gives the required product 13.

引用

页码：2243 / 2247

页数：5

共 26 条

[1] MEISENHEIMER SPIRO PICRYL COMPLEX OF ADENOSINE - AN EXAMPLE OF A STEREOSELECTIVE DIOXOLANE RING-OPENING IN AN ACIDIC MEDIUM [J].