A short path synthesis of [13C/15N] multilabeled pyrimidine nucleosides starting from glucopyranose nucleosides

被引：13

作者：

Lagoja, IM

Pochet, S

Boudou, V

Little, R

Lescrinier, E

Rozenski, J

Herdewijn, P

机构：

[1] Katholieke Univ Leuven, Rega Inst Med Res, Med Chem Lab, B-3000 Louvain, Belgium

[2] Inst Pasteur, F-75724 Paris, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 05期

关键词：

D O I：

10.1021/jo0205098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of fully [C-13/N-15] labeled pyrimidine nucleosides has been achieved from C-13-glucose and labeled nucleobases. The reaction scheme leads directly to the protected nucleosides without the need for the inversion of configuration of C-3 of C-13-glucose. This was achieved by an oxitative ring-opening reaction removing the carbon with the wrong configuration.

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页码：1867 / 1871

页数：5

相关论文

共 39 条

[21] EFFICIENT FORMATION OF PINACOLS FROM ALDEHYDES OR KETONES MEDIATED BY SAMARIUM DIIODIDE [J].

NAMY, JL ;

SOUPPE, J ;

KAGAN, HB .

TETRAHEDRON LETTERS, 1983, 24 (08) :765-766

[22] 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

[23] Synthesis of [5′-2H1]-nucleosides with defined (5′S)/(5′R)-ratios [J].

Oogo, Y ;

Ono, A ;

Ono, A ;

Kainosho, M .

TETRAHEDRON LETTERS, 1998, 39 (18) :2873-2876

[24] PRODUCTION OF FORMIC ACID DURING OXIDATION OF CARBOHYDRATES WITH LEAD TETRAACETATE [J].

PERLIN, AS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (21) :5505-5508

[25] CHEMICAL SYNTHESIS OF C-13-LABELED MONOMERS FOR THE SOLID-PHASE AND TEMPLATE CONTROLLED ENZYMATIC-SYNTHESIS OF DNA AND RNA OLIGOMERS [J].

QUANT, S ;

WECHSELBERGER, RW ;

WOLTER, MA ;

WORNER, KH ;

SCHELL, P ;

ENGELS, JW ;

GRIESINGER, C ;

SCHWALBE, H .

TETRAHEDRON LETTERS, 1994, 35 (36) :6649-6652

[26]

RHEE YS, 1993, J AM CHEM SOC, V115, P12607

[27] Studies on the SmI2-promoted pinacol-type cyclization:: Synthesis of the hexahydroazepine ring of balanol [J].

Riber, D ;

Hazell, R ;

Skrydstrup, T .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5382-5390

[28] On the reduction of some aliphatic cyano bonding - Reduction of cyano-acetyl urea [J].

Rupe, H ;

Metzger, A ;

Vogler, H .

HELVETICA CHIMICA ACTA, 1925, 8 :848-852

[29] Synthesis and NMR of RNA with selective isotopic enrichment in the bases [J].

SantaLucia, J ;

Shen, LX ;

Cai, ZP ;

Lewis, H ;

Tinoco, I .

NUCLEIC ACIDS RESEARCH, 1995, 23 (23) :4913-4921

[30]

Scott LG, 2000, METHOD ENZYMOL, V317, P18

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