Introduction of alpha-fluorophosphonomethyl ether functionality and its application to the synthesis of fluorinated acyclic phosphonate nucleosides

被引：19

作者：

Chen, W

Flavin, MT

Filler, R

Xu, ZQ

机构：

[1] MEDICHEM RES INC,LEMONT,IL 60439

[2] IIT,DEPT BIOL CHEM & PHYS SCI,CHICAGO,IL 60616

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(96)02106-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Introduction of the alpha-fluorophosphonomethyl ether functionality has been achieved by electrophilic fluorination of the corresponding phosphonomethyl ether carbanion. Coupling of the synthesized 2-[(diethoxyphosphono)fluoromethoxy]ethanol (9) with adenine and 6-chloropurine under Mitsunobu conditions afforded novel fluorinated acyclic phosphonate nucleosides 11a and 11b, respectively. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：8975 / 8978

页数：4

共 27 条

[1] SELECTIVE PROTECTION OF 1,2-DIOLS AND 1,3-DIOLS VIA ACYLATIVE CLEAVAGE OF CYCLIC FORMALS
BAILEY, WF
ZARCONE, LMJ
RIVERA, AD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) : 2532 - 2536
[2] 9-[(2RS)-3-FLUORO-2-PHOSPHONYLMETHOXYPROPYL] DERIVATIVES OF PURINES - A CLASS OF HIGHLY SELECTIVE ANTIRETROVIRAL AGENTS INVITRO AND INVIVO
BALZARINI, J
HOLY, A
JINDRICH, J
DVORAKOVA, H
HAO, Z
SNOECK, R
HERDEWIJN, P
JOHNS, DG
DECLERCQ, E
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (11) : 4961 - 4965
[3] DIALLYL (LITHIODIFLUOROMETHYL)PHOSPHONATE - A NEW REAGENT FOR THE INTRODUCTION OF THE (DIFLUOROMETHYLENE)PHOSPHONATE FUNCTIONALITY
BERKOWITZ, DB
SLOSS, DG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 7047 - 7050
[4] SYNTHESIS OF ALPHA-FLUOROVINYLPHOSPHONATES
BLACKBURN, GM
PARRATT, MJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08): : 1417 - 1424
[5] MONOFLUORO-METHYLENEBISPHOSPHONIC AND DIFLUORO-METHYLENEBISPHOSPHONIC ACIDS - ISOPOLAR ANALOGS OF PYROPHOSPHORIC ACID
BLACKBURN, GM
ENGLAND, DA
KOLKMANN, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) : 930 - 932
[6] THE SYNTHESIS AND METAL-BINDING CHARACTERISTICS OF NOVEL, ISOPOLAR PHOSPHONATE ANALOGS OF NUCLEOTIDES
BLACKBURN, GM
KENT, DE
KOLKMANN, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05): : 1119 - 1125
[7] SYNTHESIS OF ALPHA-FLUOROALKYLPHOSPHONATES AND GAMMA-FLUOROALKYLPHOSPHONATES
BLACKBURN, GM
KENT, DE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06): : 913 - 917
[8] STUDIES ON SELECTED TRANSFORMATIONS OF SOME FLUOROMETHANEPHOSPHONATE ESTERS
BLACKBURN, GM
BROWN, D
MARTIN, SJ
PARRATT, MJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01): : 181 - 186
[9] BLACKBURN GM, 1986, CHEM SCRIPTA, V26, P21
[10] ALLYLATIONS OF [(DIETHOXYPHOSPHINYL)DIFLUOROMETHYL]ZINC BROMIDE AS A CONVENIENT ROUTE TO 1,1-DIFLUORO-3-ALKENEPHOSPHONATES
BURTON, DJ
SPRAGUE, LG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) : 613 - 617

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