Synthesis of 2′-deoxy-2-fluoro-1-β-D-arabinofuranosyl uracil derivatives:: A method suitable for preparation of [18F]-labeled nucleosides

被引：10

作者：

Alauddin, MM

Conti, PS

Fissekis, JD

Watanabe, KA

机构：

[1] Univ So Calif, PET Imaging Sci Ctr, Los Angeles, CA 90033 USA

[2] Mem Sloan Kettering Canc Ctr, Organ Chem Lab, New York, NY 10021 USA

来源：

SYNTHETIC COMMUNICATIONS | 2002年 / 32卷 / 11期

关键词：

D O I：

10.1081/SCC-120004272

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-glycosylation of 2,4-bis-O-(trimethylsilyl)-pyrimidine bases with 2-deoxy-2-fluoro-3,5-di-O-benzoyl-1-(Br, OBz)-alpha-D-arabinose derivatives are reported. I-Bromo-arabinose provides high yield and a favorable anomeric ratio (beta/alpha) of pyrimidine nucleoside in either MeCN or CH2Cl-CH2Cl. This method should be suitable for the synthesis of 2'-deoxy-2-[F-18]fluoro-1-beta-D-arabinofuranosyluracil derivatives.

引用

收藏

页码：1757 / 1764

页数：8

相关论文

共 12 条

[1] Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters:: preparation of a versatile intermediate for synthesis of 2′-[18F]-fluoro-arabinonucleosides [J].

Alauddin, MM ;

Conti, PS ;

Mathew, T ;

Fissekis, JD ;

Prakash, GKS ;

Watanabe, KA .

JOURNAL OF FLUORINE CHEMISTRY, 2000, 106 (01) :87-91

[2]

Bading JR, 2000, J NUCL MED, V41, p234P

[3] Triethylamine poly(hydrogen fluorides) in the synthesis of a fluorinated nucleoside glycon [J].

Chou, TS ;

Becke, LM ;

OToole, JC ;

Carr, MA ;

Parker, BE .

TETRAHEDRON LETTERS, 1996, 37 (01) :17-20

[4]

Conti P. S., 1996, Journal of Nuclear Medicine, V37, p107P

[5] SYNTHESIS OF 2'-FLUORO-5-[C-11]-METHYL-1-BETA-D-ARABINOFURANOSYLURACIL ([C-11]-FMAU) - A POTENTIAL NUCLEOSIDE ANALOG FOR IN-VIVO STUDY OF CELLULAR PROLIFERATION WITH PET [J].

CONTI, PS ;

ALAUDDIN, MM ;

FISSEKIS, JR ;

SCHMALL, B ;

WATANABE, KA .

NUCLEAR MEDICINE AND BIOLOGY, 1995, 22 (06) :783-789

[6] ANTIVIRAL NUCLEOSIDES - A STEREOSPECIFIC, TOTAL SYNTHESIS OF 2'-FLUORO-2'-DEOXY-BETA-D-ARABINOFURANOSYL NUCLEOSIDES [J].

HOWELL, HG ;

BRODFUEHRER, PR ;

BRUNDIDGE, SP ;

BENIGNI, DA ;

SAPINO, C .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :85-88

[7] AN INVESTIGATION BY H-1-NMR SPECTROSCOPY INTO THE FACTORS DETERMINING THE BETA-ALPHA RATIO OF THE PRODUCT IN 2'-DEOXYNUCLEOSIDE SYNTHESIS [J].

HUBBARD, AJ ;

JONES, AS ;

WALKER, RT .

NUCLEIC ACIDS RESEARCH, 1984, 12 (17) :6827-6837

[8] SYNTHESIS OF NUCLEOSIDES .9. GENERAL SYNTHESIS OF N-GLYCOSIDES .1. SYNTHESIS OF PYRIMIDINE NUCLEOSIDES [J].

NIEDBALLA, U ;

VORBRUGGEN, H .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (25) :3654-3660

[9] NUCLEOSIDES .146. 1-METHYL-5-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)URACIL, THE C-NUCLEOSIDE ISOSTERE OF THE POTENT ANTIVIRAL AGENT 1-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)THYMINE (FMAU) - STUDIES DIRECTED TOWARD THE SYNTHESIS OF 2'-DEOXY-2'-SUBSTITUTED ARABINO NUCLEOSIDES .6. [J].

PANKIEWICZ, KW ;

NAWROT, B ;

GADLER, H ;

PRICE, RW ;

WATANABE, KA .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (12) :2314-2316

[10] PRACTICAL SYNTHESIS OF 2-DEOXY-2-FLUORO-D-ARABINOFURANOSE DERIVATIVES [J].

REICHMAN, U ;

WATANABE, KA ;

FOX, JJ .

CARBOHYDRATE RESEARCH, 1975, 42 (02) :233-240