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THE SYNTHESIS OF NOVEL CARBOHYDRATES AMENABLE TO THE SYNTHESIS OF 2',3'-DIDEOXY-3'-BRANCHED NUCLEOSIDES

被引：7
作者：
PUDLO, JS
TOWNSEND, LB
机构：
[1] UNIV MICHIGAN,COLL LITERATURE SCI & ARTS,DEPT CHEM,ANN ARBOR,MI 48109
[2] UNIV MICHIGAN,COLL PHARM,DEPT MED CHEM,ANN ARBOR,MI 48109
来源：
NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 2-4期
基金：
美国国家卫生研究院;
关键词：
D O I：
10.1080/07328319208021703
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The facile synthesis of several substituted carbohydrates that are amenable for the preparation of 2',3'-dideoxy-3'-hydroxymethyl nucleosides are reported. Elaboration of a previously reported analog, 5-O-benzoyl-3-deoxy-3-(benzyloxy)methyl-1,2-O-isopropylidene-alpha-D-ribofuranose (4) has provided two 2,3-dideoxy-3-branched ribose derivatives 5-O-benzoyl-2,3-dideoxy-3-(benzyloxy)methyl-1-O-methyl-beta-ribofuranose (7) and 1,5-di-O-benzoyl-2,3-dideoxy-3-(benzyloxy)methyl-(alpha,beta)-D-ribofuranose (10). Due to problems involved with the separation of anomeric mixtures when these carbohydrates were condensed with an heterocycle, another versatile synthon 5-O-benzoyl-3-deoxy-3-(benzyloxy)methyl-2-O-t-butyldimethylsilyl-1-O-methyl-beta-D-ribofuranose (12) was synthesized. The utility of this compound (12) is demonstrated in the total synthesis of 1-[3-deoxy-3-hydroxymethyl-beta-D-ribofuranosyl]thymine (20).
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页码：279 / 293
页数：15
相关论文
共 12 条
[1]   IMPROVED ANTI-TUMOR EFFECTS IN 3'-BRANCHED HOMOLOGS OF 2'-DEOXYTHIOGUANOSINE - SYNTHESIS AND EVALUATION OF THIOGUANINE NUCLEOSIDES OF 2,3-DIDEOXY-3-(HYDROXYMETHYL)-D-ERYTHRO-PENTOFURANOSE [J].
ACTON, EM ;
GOERNER, RN ;
UH, HS ;
RYAN, KJ ;
HENRY, DW ;
CASS, CE ;
LEPAGE, GA .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (05) :518-525
[2]   SYNTHESIS AND ANTIVIRAL ACTIVITY OF 3'-DEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES [J].
BAMFORD, MJ ;
COE, PL ;
WALKER, RT .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2494-2501
[3]   THE X-RAY STRUCTURE DETERMINATION OF OXETANOCIN [J].
NAKAMURA, H ;
HASEGAWA, S ;
SHIMADA, N ;
FUJII, A ;
TAKITA, T ;
IITAKA, Y .
JOURNAL OF ANTIBIOTICS, 1986, 39 (11) :1626-1629
[4]   SYNTHESIS OF OLIGORIBONUCLEOTIDES .2. USE OF SILYL PROTECTING GROUPS IN NUCLEOSIDE AND NUCLEOTIDE CHEMISTRY .7. [J].
OGILVIE, KK ;
BEAUCAGE, SL ;
SCHIFMAN, AL ;
THERIAULT, NY ;
SADANA, KL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (21) :2768-2780
[5]  
PUDLO JS, 1990, TETRAHEDRON LETT, V31, P3104
[6]   BRANCHED-CHAIN SUGAR NUCLEOSIDES .4. 9-(3-DEOXY-3-C- HYDROXYMETHYL -BETA(AND ALPHA)-D-ALLOFURANOSYL AND RIBOFURANOSYL)ADENINE [J].
ROSENTHAL, A ;
SPRINZL, M .
CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1969, 47 (23) :4477-+
[7]  
ROU KUB, 1986, NUCLEOS NUCLEOT, V5, P539
[8]   CHEMICAL CONVERSION OF URIDINE TO 3'-BRANCHED SUGAR NUCLEOSIDES (NUCLEOSIDES AND NUCLEOTIDES .42. [J].
SHUTO, S ;
IWANO, T ;
INOUE, H ;
UEDA, T .
NUCLEOSIDES & NUCLEOTIDES, 1982, 1 (03) :263-273
[9]   SYNTHESIS AND ANTIVIRAL EVALUATION OF 3'-BRANCHED NUCLEOSIDE ANALOGS [J].
STERZYCKI, RZ ;
MARTIN, JC ;
WITTMAN, M ;
BRANKOVAN, V ;
YANG, H ;
HITCHCOCK, MJ ;
MANSURI, MM .
NUCLEOSIDES & NUCLEOTIDES, 1991, 10 (1-3) :291-294
[10]   SYNTHESIS OF 2',3'-DIDEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES AS POTENTIAL INHIBITORS OF HIV [J].
SVANSSON, L ;
KVARNSTROM, I ;
CLASSON, B ;
SAMUELSSON, B .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2993-2997
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