OXIDATIVE CYCLIZATION OF 2',3'-O-ISOPROPYLIDENE-ADENOSINES INTO 5'-O,8-CYCLOADENOSINES WITH LEAD-TETRAACETATE - REMARKABLE EFFECT OF N6-SUBSTITUENTS ON THE OXIDATION

被引：7

作者：

KITADE, Y ^{[1
]}

MAKINO, T ^{[1
]}

HIROTA, K ^{[1
]}

MAKI, Y ^{[1
]}

机构：

[1] GIFU PHARMACEUT UNIV,DEPT MED CHEM,5-6-1 MITAHORA HIGASHI,GIFU 502,JAPAN

来源：

NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 2-4期

关键词：

D O I：

10.1080/07328319208021710

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：

Oxidation of 2',3'-O-isopropylideneadenosines (1) with lead tetraacetate (LTA) in dry benzene resulted in the formation of the corresponding 5'-O,8-cyclo-2',3'-O-isopropylideneadenosines (2), which has a new methodological implication for the chemical modification of adenosines. The occurrence of the oxidative cyclization was remarkably affected by the nature of N6-substituents: N6-benzoyl substitution prominently accelerated the oxidative cyclization in comparison with none and dimethyl substitutions. In the oxidation of N6,N6-dimethyladenosine (1d), an intriguing oxidative demethylation was observed.

引用

页码：365 / 372

页数：8

共 7 条

[1] THE PROMINENT EFFECT OF N6-ACYL GROUPS ON THE REACTIVITY OF 5'-O,8-CYCLOADENOSINES - AN APPLICATION TO THE SYNTHESIS OF 2-SUBSTITUTED ADENOSINES
MAKI, Y
SAKO, M
SAITO, T
KAMEYAMA, K
HIROTA, K
JOURNAL OF PHARMACEUTICAL SCIENCES, 1987, 76 (11) : S223 - S223
[2] A NOVEL STEREOSPECIFIC RADICAL CYCLIZATION OF 2',3'-O-ISOPROPYLIDENEURIDINE AND 2',3'-O-ISOPROPYLIDENE-ADENOSINE 5'-ALDEHYDE TO THE CORRESPONDING 6,5'-CYCLODIHYDROURIDINE AND 8,5'-CYCLOADENOSINE DERIVATIVES
SUGAWARA, T
OTTER, BA
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TETRAHEDRON LETTERS, 1988, 29 (01) : 75 - 78
[3] The effect of various substituents on the structural parameters of the P(O)[N(CH3)(CH2C6H5)]2 moiety.: Syntheses and spectroscopic characterization of some new phosphoramidates, crystal structures of P(O)(X)[N(CH3)(CH2C6H5)]2, X = C6H5C(O)NH, Cl and CCl3C(O)NH
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Pourayoubi, M
Shariatinia, Z
Mostaanzadeh, H
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[4] Synthesis and crystal structure of a novel lead coordination polymer, [[Pb3(C8H3O7S)2(C3H7NO)2.5(H2O)]•1.5H2O]n, C47H57N5O38Pb6S4
Zhao, Hua-Yi
Zhang, Xue-Juan
Li, Xin-Hua
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2012, 227 (03): : 419 - 421
[5] Ab-initio study of effect of basic MgO to V2O5 catalyst on oxidative dehydrogenation of C3H8 and n-C4H10
Nguyen Ngoc Ha
Ngo Duc Huyen
Le Minh Cam
APPLIED CATALYSIS A-GENERAL, 2011, 407 (1-2) : 106 - 111
[6] Rigidity and/or flexibility of calixarenes.: Effect of the p-sulfonatocalix[n]arenes (n=4, 6, and 8) on the electron transfer process [Ru(NH3)5pz]2++Co(C2O4)33-
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Muriel, F.
Lopez-Cornejo, P.
JOURNAL OF PHYSICAL CHEMISTRY B, 2007, 111 (36): : 10697 - 10702
[7] Crystal structure of (2-(4-fluorophenyl)-1H-imidazo[4,5-f][1,10]-phenanthroline)-(5-nitro-1,3-benzenedicarboxylato)lead(II) sesquihydrate, Pb(C19H11N4F)2(C8H3NO6) • 1.5H2O
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