Studies towards the Synthesis of the Fluorescent Bases of Phenylalanine Transfer Ribonucleic Acids : Synthesis of 7-Methylwye Isolated from Extremely Thermophilic Archaebacteria
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概要
- 論文の詳細を見る
Acid- or base-catalyzed acylation of 1-benzylwye (7) provided the 7-substituted derivatives 9,10,and 11 in poor yields. Although the reactions of lithiated 7 with electrophiles gave the 2-substituted derivatives 14,15,17,20,21,and 22,lithiation of 1-benzyl-7-bromo-2-chlorowye (23) followed by treatment with Me_2CHCH_2CHO (13) successfully introduced a side chain at the 7-position to afford 1-benzyl-2-chloro-7-(1-hydroxy-3-methylbutyl)wye (24).Cyclization of 1-benzyl-3-methylguanine (5) with 3-bromo-2-butanone followed by catalytic hydrogenolysis afforded 7-methylwye (2b), the hypermodified base isolated from archaebacterial transfer ribonucleic acids. A more efficient route for the synthesis of 2b has been developed via a series of reactions : the Vilsmeier-Haack reaction of 7,reduction with NaBH_4,and catalytic hydrogenolysis over Pd-C.
- 公益社団法人日本薬学会の論文
- 1989-02-25
著者
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板谷 泰助
Faculty of Pharmaceutical Sciences, Kanazawa University
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板谷 泰助
金沢大学薬学部
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水谷 朱見
Faculty of Pharmaceutical Sciences, Kanazawa University
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水谷 朱見
Faculty Of Pharmaceutical Sciences Kanazawa University
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竹田 資子
Faculty of Phamaceutical Sciences, Kanazawa University
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塩山 智栄子
Faculty of Phamaceutical Sciences, Kanazawa University
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竹田 資子
Faculty Of Pharmaceutical Sciences Kanazawa University
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塩山 智栄子
Faculty Of Phamaceutical Sciences Kanazawa University
関連論文
- Purines. LXX. An Extension of the "Phenacylamine Route" to the Syntheses of the 7-N-Oxides of 6-Mercaptopurine and 6-Methylthiopurine, and Antileukemic Activity of Some Purine N-Oxides
- Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
- Purines. LXVIII. Trifluoroperoxyacetic Acid Oxidation of N^6-Benzyladenine : Formation of the N(3)-Oxide and N(7)-Oxide, and Their Cytokinin Activities
- Purines. LXVII. An Alternative Synthesis of Adenine 7-Oxide : N-Oxidation of the Adenine Ring Utilizing Blocking/Deblocking at the 1-Position
- Purines. LXVI. Adenine 7-Oxide : Its Synthesis, Chemical Properties, and X-ray Molecular Structure
- Purines. LII. Synthesis and Biological Evaluation of 8-Methylguanine 7-Oxide and Its 9-Arylmethyl Derivatives
- Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
- Purines. L. Synthesis and Antileukemic Activity of the Antibiotic Guanine 7-Oxide and Its 9-Substituted Derivatives
- FORMATION OF CYCLIC CARBONATES IN THE REACTIONS OF 1,2-GLYCOLS WITH OXALYL CHLORIDE
- Purines. XXI. Synthesis of Adenine 1-Oxides Carrying an Allylic Side Chain at the 9-Position
- Synthesis of 3-β-D-Ribofuranosylwye, the Most Probable Structure for Wyosine from Torulopsis utilis Phenylalanine Transfer Ribonucleic Acid
- Synthesis of 5-(Methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide, a Synthetic Intermediate for 3-Methyl-9-β-D-ribofuranosylpurines
- An Improved Procedure for the Synthesis of 1-Alkyl-5-(alkylamino)-imidazole-4-carboxamides, Synthetic Intermediates for 3,9-Dialkylpurine Derivatives
- Synthesis of N, N, 3,9-Tetraalkyladeninium Halides by Alkylations of N, N, 3- and N, N, 9-Trialkyladenines
- Purines. XXXV. : Synthesis and Cytokinin Activity of Racemic 1'-Methylzeatin
- Purines. XXXIII. Syntheses and Cytokinin Activities of Both Enantiomers of 1'-Methylzeatin and Their 9-β-D-Ribofuranosides
- Studies towards the Synthesis of the Fluorescent Bases of Phenylalanine Transfer Ribonucleic Acids : Synthesis of 7-(2-Hydroxy-3-methylbutyl)wye, a Model for the Minor Base Isolated from Rat Liver
- Purines. XIX. The Direct N^6-Alkylation of 1-Alkoxy-9-alkyladenines : An Alternative Synthesis of N^6,9-Dialkyladenines
- Wittig Reaction with N-Protected 3-(Triphenylphosphonio)alaninates : Synthesis of Optically Active (E)-(2-Arylvinyl)glycine Derivatives
- Synthesis and Absolute Configuration of Wybutine, the Fluorescent Minor Base from Phenylalanine Transfer Ribonucleic Acids
- Purines. XLVI. Preparation of 1-Ethyladenine from Adenosine
- 3,9-Dialkylhypoxanthines
- Purines. V. The Dimroth Rearrangement of 1-Alkoxyadenines : The Synthesis of N-Alkoxyadenines
- Synthesis of 5-(Alkylamino)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamides : Key Intermediates for the Synthesis of 3-Alkyl-9-β-D-ribofuranosylpurine Derivatives
- Purines. XXXII. : Synthesis and Ring Fission of 3,9-Dialkyladenines
- Purines. XXIX. Syntheses of 9-Alkyl-2-deuterio-N^6-methoxyadenines and 2-Deuterio-N^6,9-dimethyladenine : Tautomerism in 9-Substituted N^6-Alkoxyadenines(Organic,Chemical)
- Purines. XXV. Fission and Reclosure of the Adenine Ring by the Use of Modified Benzyloxy Groups at the 1-Position
- Purines. XXII. Methylation of 1-, 3-, 7-, 9-, and N^6-Methyladenines Bearing a Methoxyl Group at the N^6-Position : A Synthesis of 7,9-Dimethyladenine
- Purines. XX. Synthesis of 1-Substituted 5-Aminoimidazole-4-carboxamidines and Related Compounds
- Syntheses of N, N, 3- and N, N, 9-Trialkyladenines by Alkylation of N, N-Dialkyladenines
- Studies towards the Synthesis of the Fluorescent Bases of Phenylalanine Transfer Ribonucleic Acids : Synthesis of 7-Methylwye Isolated from Extremely Thermophilic Archaebacteria
- Ind. -N-Alkylation of Tryptophan and Synthesis of 1-Alkyltryptophan Hydrazides
- フェニルアラニン転移リボ核酸超修飾ヌクレオシドの合成をめぐって
- The Heck Reaction of N-Protected Vinylglycines with 4-Iodoanisole
- Syntheses of Optically Active, Protected and Unprotected Vinylglycines
- 3-Methylisoguanosine : Synthesis and Acidic Hydrolysis of the Glycosyl Bond
- Synthesis of 7-Methyl-3-β-D-ribofuranosylwye, the Putative Structure for the Hypermodified Nucleoside Isolated from Archaebacterial Transfer Ribonucleic Acids
- An Improved Procedure for the Synthesis of 1-Alkyladenines : Removal of the Ribofuranosyl Group from 1-Benzyl-, 1-(3-Methyl-2-butenyl)-, and 1-Allyladenosine Hydrobromide in Acetic Acid
- Purines. XV. Conversion of N, 9-Dimethyladenine into the 1,9-Dimethyl Isomer : A Reverse Operation of the Dimroth Rearrangement
- Improved Synthesis of 3-Methylguanine
- Purines. X. A Convenient Method for Synthesis of 2', 3'-O-Isopropylidene-adenosine 1-Oxide
- アデニン環の開裂と再閉環
- Purines. XVIII. Kinetic Studies of the Dimroth Rearrangement of 1-Alkoxy-9-methyladenines and 1-Benzyloxyadenosine : Effect of 1-Benzyloxy and 9-β-D-Ribofuranosyl Groups on the Rates of the Ring-opening and the Reclosure
- Purines. XVI. One-Step Alkylation of Adenine 1-Oxide Leading to 1-Alkoxy-9-alkyladenine Hydriodide
- 3-Methylxanthosine : Synthesis and Acidic Hydrolysis of the Glycosyl Bond
- 転移リボ核酸微量成分の合成化学的研究
- SYNTHESIS OF 7-METHYL-3-β-D-RIBOFURANOSYLWYE, THE MOST PROBABLE STRUCTURE FOR THE FLUORESCENT NUCLEOSIDE ISOLATED FROM ARCHAEBACTERIAL TRANSFER RIBONUCLEIC ACIDS(Communications to the Editor)
- 転移リボ核酸の修飾成分
- 3-Methylinosine
- 不老不死の薬(薬学第二世紀の出発点に立って)
- Purines. XII. Catalytic Hydrogenolysis of Alkoxyaminopurines and Related Derivatives
- Purines. XI. The Synthesis of N-Alkoxyadenosines and Their 2', 3'-O-Isopropylidene Derivatives
- Purines. IX. Deoxygenation of 1-Benzyloxyadenine Derivatives : The Formation of Benzaldehyde
- Purines. VII. 1-Alkoxy-9-alkyladenine Salts as Possible Alkylating Reagents