141684-87-9Relevant academic research and scientific papers
Nucleic acid related compounds. 105. Synthesis of 2',3'-didehydro- 2',3'-dideoxynucleosides from ribonucleoside cyclic 2',3'-(Sulfates or phosphates) or 2',3'-dimesylates via reductive elimination with sodium naphthalenide
Robins, Morris J.,Lewandowska, Elzbieta,Wnuk, Stanislaw F.
, p. 7375 - 7381 (2007/10/03)
Treatment of purine ribonucleosides with thionyl fluoride resulted in formation of cyclic 2',3'-sulfite esters. Acetylation of the 5'-hydroxy group and Sharpless oxidation (NaIO4/RuCl3) gave the cyclic 2',3'-sulfate ester derivatives. Treatment of 5'-O-silyl-protected ribonucleosides with thionyl chloride followed by oxidation gave an alternative route to the cyclic 2',3'- sulfates. Reductive elimination with sodium naphthalenide (THF/-50 °C) gave the 2',3'-unsaturated nucleosides. Parallel treatment of adenosine cyclic 2',3'-phosphate gave the 2',3'-olefin. The adenine, hypoxanthine, and 2- amino-6-methoxypurine 2',3'-didehydro-2',3'-dideoxynucleosides were prepared efficiently (40-60% overall yields of crystalline, analytically pure products; 3-5 steps, some combined into one-flask procedures) by treatment of 5'-O-protected 2',3'-di-O-mesylribonucleosides with sodium naphthalenide. Reactions were performed at or below ambient temperature with readily available reagents and standard laboratory conditions.
Uracil and Adenine Nucleosides Having a 2',3'-Bromovinyl Structure: Highly Versatile Synthons for the Synthesis of 2'-C- and 3'-C-Branched 2',3'-Unsaturated Derivatives
Haraguchi, Kazuhiro,Itoh, Yoshiharu,Tanaka, Hiromichi,Akita, Mitsuhiro,Miyasaka, Tadashi
, p. 1371 - 1390 (2007/10/02)
Preparation of 2'- and 3'-bromo derivatives of 2',3'-unsaturated uracil and adenine nucleosides has been carried out starting from the corresponding β-hydroxyselenides by way of bromination and successive selenoxide elimination.These compounds have been shown to serve as versatile synthons for the preparation of anti-HIV candidates, 2'-C- and 3'-C-branched 2',3'-unsaturated nucleosides, through palladium-catalyzed cross-coupling and halogen-lithium exchange reactions. Key Words: β-hydroxyselenide; bromovinyl structure; branched-sugar nucleoside; anti-HIV agent; 2',3'-unsaturated nucleoside.
A Highly Stereoselective Synthesis of Anti-HIV 2',3'-Dideoxy- and 2',3'-Didehydro-2',3'-dideoxynucleosides
Beach, J. Warren,Kim, Hea O.,Jeong, Lak S.,Nampalli, Satyanarayana,Islam, Qamrul,et al.
, p. 3887 - 3894 (2007/10/02)
A general total synthesic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented.Introduction of an α-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give >/=95percent β-isomer.This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine.The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.
