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
收藏
页码：823 / 826
页数：4
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