SYNTHESIS OF 3'-(N-ACETYLPIPERAZINO)-2',3'-DIDEOXY-D-RIBO-HEXOFURANOSYL AND 3'-(N-ACETYLPIPERAZINO)-2',3'-DIDEOXY-D-RIBO-HEXOFURANOSYL-D-ERYTHRO-PENTOFURANOSYL THYMINE NUCLEOSIDES

被引：0

作者：

PETERSEN, GV

PLATZ, J

NIELSEN, C

WENGEL, J

机构：

[1] ODENSE UNIV,DEPT CHEM,DK-5230 ODENSE M,DENMARK

[2] STATENS SERUM INST,DEPT VIROL,RETROVIRUS LAB,DK-2300 COPENHAGEN,DENMARK

来源：

SYNTHESIS-STUTTGART | 1994年 / 08期

关键词：

ALPHA; BETA-UNSATURATED ALDEHYDE; MICHAEL-TYPE ADDITION; N-ACETYLPIPERAZINE; VORBRUGGEN CONDENSATION; DIOL CLEAVAGE;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael-type addition of N-acetylpiperazine to the cc,P-unsaturated hexose aldehyde 1 in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gave an anomeric mixture of 3-(N-acetylpiperazino)-2,3-dideoxy-D-ribo-hexofuranoses, which was acetylated to give the tri-O-acetyl derivative 2. Reaction of 2 with silylated thymine 5 using trimethylsilyl trifluoromethanesulfonate as catalyst gave the hexofuranose nucleosides 6 and 7. The pure anomers were deprotected using a saturated solution of NH, in dry MeOH affording 8 and 9. Conversion of 8 and 9 into the corresponding pentofuranose nucleosides 10 and 11 was accomplished by periodate oxidative cleavage and subsequent reduction.

引用

页码：823 / 826

页数：4

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