Stereoselective conversion of 2′,3′-dideoxydidehydro carbocyclic nucleosides into 2′-deoxy carbocyclic nucleosides

被引：3

作者：

Barkley, JV

Dhanda, A

Knutsen, LJS

Nielsen, MB

Roberts, SM

Varley, DR

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

[2] Novo Nordisk AS, DK-2760 Malov, Denmark

[3] Univ Exeter, Dept Chem, Exeter EX4 4QD, Devon, England

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 10期

关键词：

D O I：

10.1039/a801759j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of 2',3'-dideoxydidehydro carbocyclic nucleosides 5-9 with N-bromoacetamide in AcOH gives bromoesters 10-14 with good stereocontrol: debromination and hydrolysis furnishes 2'-deoxy carbocyclic nucleosides, e.g. 22.

引用

页码：1117 / 1118

页数：2

共 16 条

[1] Asymmetric total synthesis of (+)-carbocyclic uracil polyoxin C [J].

Aggarwal, VK ;

Monteiro, N .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (17) :2531-2537

[2]

[Anonymous], 2004, ORGANIC CHEM DRUG DE

[3] Nucleosides and nucleotides .153. Effects of 2'-alpha- and 2'-beta-bromo-2'-deoxyadenosine on oligonucleotide hybridization and nuclease stability [J].

Aoyagi, M ;

Ueno, Y ;

Ono, A ;

Matsuda, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (13) :1573-1576

[4] ENANTIOSELECTIVE PREPARATION OF FUNCTIONALIZED CYCLOPENTANOIDS VIA A COMMON CHIRAL (PI-ALLYL)PALLADIUM COMPLEX [J].

DEARDORFF, DR ;

LINDE, RG ;

MARTIN, AM ;

SHULMAN, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2759-2762

[5]

KATAGIRI N, 1994, CHEM PHARM BULL, V42, P2653

[6] THE CHEMISTRY OF 2'-DEOXYRIBO-C-NUCLEOSIDES [J].

KNUTSEN, LJS .

NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (05) :961-983

[7]

MARUMOTO R, 1976, CHEM PHARM BULL, V24, P2624

[8] Practical enantiodivergent syntheses of both enantiomers of carbovir, 1592U89 and six-membered ring analogues [J].

Olivo, HF ;

Yu, JX .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03) :391-392

[9] Enantioselective syntheses of 5'-homo-carbocyclic nucleosides [J].

Olivo, HF ;

Yu, JX .

TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3785-3788

[10] Unexpected stereoselectivity in the cis dihydroxylation of some 2-cyclopentene-1-carboxamides. [J].

Palmer, CF ;

McCague, R ;

Ruecroft, G ;

Savage, S ;

Taylor, SJC ;

Ries, C .

TETRAHEDRON LETTERS, 1996, 37 (26) :4601-4604

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