GENERAL METHOD OF SYNTHESIS AND ISOLATION, AND AN NMR-SPECTROSCOPIC STUDY, OF "TETRA-O-ACETYL-D-ALDOPENTOFURANOSES

被引：93

作者：

KAM, BL ^{[1
]}

BARASCUT, JL ^{[1
]}

IMBACH, JL ^{[1
]}

机构：

[1] UNIV MONTPELLIER 2,CHIM BIOORGAN LAB,F-34060 MONTPELLIER,FRANCE

来源：

CARBOHYDRATE RESEARCH | 1979年 / 69卷 / MAR期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0008-6215(00)85758-4

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 Guthrie-Smith method for the synthesis of tetra-O-acetyl-β-d-ribofuranose has been successfully generalized to apply to the d-aldopentofuranose series. Treament of a d-aldopentose with acidic methanol, followed by acetylation and acetolysis, led to the peracetylated derivatives in good yields. All compounds were characterized, and their structures established. Isolation of products is described, and their 1H- and 13C-n.m.r. spectra are discussed. © 1979.

引用

页码：135 / 142

页数：8

共 22 条

[1] PUROMYCIN - SYNTHETIC STUDIES .13. SYNTHESIS OF 6-DIMETHYLAMINO-9-(3'-AMINO-3'-DEOXY-BETA-D-ARABINOFURANOSYL)-PURINE
BAKER, BR
SCHAUB, RE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (22) : 5900 - 5905
[2] REACTION OF ACYLATED METHYL ARABINOSIDES WITH HYDROGEN BROMIDE
BOCK, K
PEDERSEN, C
[J]. CARBOHYDRATE RESEARCH, 1973, 29 (02) : 331 - 338
[3] STUDY OF CH-13 COUPLING-CONSTANTS IN PENTOPYRANOSES AND SOME OF THEIR DERIVATIVES
BOCK, K
PEDERSEN, C
[J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, B 29 (02): : 258 - 264
[4] COMPLETE ASSIGNMENT OF C-13 NMR-SPECTRUM OF MUTA-ROTATED D-RIBOSE BY INTEGRATION AND SPECIFIC DEUTERATION
BREITMAIER, E
HOLLSTEIN, U
[J]. ORGANIC MAGNETIC RESONANCE, 1976, 8 (11): : 573 - 575
[5] EXPERIMENTS ON THE SYNTHESIS OF PURINE NUCLEOSIDES .25. 1-2-3-5-TETRA-ACETYL D-ARABOFURANOSE AND THE D-ARABOFURANOSIDES OF THEOPHYLLINE AND ADENINE
BRISTOW, NW
LYTHGOE, B
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1949, (SEP): : 2306 - 2309
[6] Brown G.B., 1955, BIOCH PREP, V4, P70
[7] EXPERIMENTS ON THE SYNTHESIS OF PURINE NUCLEOSIDES .27. 1-2-3-5-TETRA-ACETYL D-XYLOFURANOSE AND THE D-XYLOFURANOSIDES OF THEOPHYLLINE AND ADENINE
CHANG, P
LYTHGOE, B
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1950, (AUG): : 1992 - 1993
[8] CHRISTL M, 1971, J AM CHEM SOC, V93, P3463, DOI 10.1021/ja00743a028
[9] FURTHER STUDIES ON ASSIGNMENT OF SIGNALS IN C-13 MAGNETIC-RESONANCE SPECTRA OF ALDOSES AND DERIVED METHYL GLYCOSIDES
GORIN, PAJ
MAZUREK, M
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (08): : 1212 - 1223
[10] GUTHRIE RD, 1968, CHEM IND-LONDON, P547

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