ChemInform Abstract: NUCLEIC ACID RELATED COMPOUNDS. 34. NON-AQUEOUS DIAZOTIZATION WITH TERT-BUTYL L NITRITE. INTRODUCTION OF FLUORINE, CHLORINE, AND BROMINE AT C-2 OF PURINE NUCLEOSIDES

1982 ◽  
Vol 13 (4) ◽  
Author(s):  
M. J. ROBINS ◽  
B. UZNANSKI
Keyword(s):  
Nucleic Acid ◽  
Tert Butyl ◽  
Related Compounds

Nucleic acid related compounds. 34. Non-aqueous diazotization with tert-butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleosides

1981 ◽  
Vol 59 (17) ◽  
pp. 2608-2611 ◽  
Author(s):  
Morris J. Robins ◽  
Bogdan Uznański
Keyword(s):  
Nucleic Acid ◽  
Hydrogen Fluoride ◽  
Antimony Trichloride ◽  
Anhydrous Ammonia ◽  
Pyridine Hydrochloride ◽  
Tert Butyl ◽  
Anhydrous Hydrogen Fluoride ◽  
Related Compounds

Treatment of 2,6-diamino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (1c) with tert-butyl nitrite (TBN) in 60% anhydrous hydrogen fluoride/pyridine at −20 °C gave 2-fluoroadenosine triacetate (2) in 48% yield. Analogous treatment of the acetylated 2-amino-6-fluoropurine nucleoside (1a) gave the 2,6-difluoro compound (3a) in 63% yield. Anhydrous ammonia in 1,2-dimethoxy-ethane converted 3a → 2 without ammonolysis of the acetate groups. The overall conversion of 1a → 3a → 2 without isolation of 3a proceeded in 80% yield. Similar diazotization of the 2-amino-6-chloro nucleoside (1b) in HF/pyridine gave the 2-fluoro-6-chloro analogue (3b) in 89% yield. Treatment of 1b with TBN and pyridine hydrochloride in dichloromethane (77%) or TBN and antimony trichloride in 1,2-dichloroethane (84%) gave the 2,6-dichloropurine nucleoside (4b). The latter conditions converted 1a to the 2-chloro-6-fluoro product (4a) in 77% yield. Conversions of 1a and 1b to the 2-bromo-6-fluoro (5a, 67%) and 2-bromo-6-chloro (5b, 78%) analogues were effected using TBN and antimony tribromide in dibromomethane.

scholarly journals THE ASSIMILATION OF NUCLEIC ACID DERIVATIVES AND RELATED COMPOUNDS BY YEASTS

1951 ◽  
Vol 189 (1) ◽  
pp. 151-157 ◽  
Author(s):  
Frederick J. Di Carlo ◽  
Alfred S. Schultz ◽  
Doris K. McManus
Keyword(s):  
Nucleic Acid ◽  
Related Compounds

Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides

1983 ◽  
Vol 26 (5) ◽  
pp. 661-666 ◽  
Author(s):  
Erik De Clercq ◽  
Johan Descamps ◽  
Jan Balzarini ◽  
Jerzy Giziewicz ◽  
Philip J. Barr ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Biological Activities ◽  
Related Compounds

Nucleic Acid Related Compounds. 5. The Transformation of Formycin and Tubercidin into 2′- and 3′-Deoxynucleosides

1973 ◽  
Vol 51 (9) ◽  
pp. 1313-1321 ◽  
Author(s):  
Morris J. Robins ◽  
James R. McCarthy Jr. ◽  
Roger A. Jones ◽  
Rudolf Mengel
Keyword(s):  
Nucleic Acid ◽  
Mass Spectra ◽  
Sodium Iodide ◽  
Excess Sodium ◽  
Related Compounds

Reaction of tubercidin (4-amino-7-β-D-ribofuranosylpyrrolo[2,3-d]pyrimidine) (1) with α-acetoxyisobutyryl chloride in the presence of excess sodium iodide in acetonitrile gave an acylated iodo intermediate (2) which was converted into 3′-deoxytubercidin (4) by hydrogenolysis and subsequent saponification.Analogous treatment of formycin (7-amino-3-β-D-ribofuranosylpyrazolo[4,3-d]pyrimidine) (5) gave 3′-deoxyformycin (6) and 2′-deoxyformycin (7) in an approximate ratio of 3:2. These purified nucleosides, 6 and 7 were individually deaminated enzymatically to give 3′-deoxyformycin B (8) and 2′-deoxyformycin B(9).Biological rationale, n.m.r., and mass spectra of these antibiotic-derived deoxynucleosides are discussed.

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