Friedel–Crafts Alkylation with Carbenium Ions Generated by Electrochemical Oxidation of Stannylmethyl Ethers
The electrochemical activation of stannylmethyl ethers was exploited for Friedel–Crafts alkylation of arenes at near-neutral conditions. Single cell anodic oxidation of stannylmethyl ethers leads to oxonium ions which fragment to carbenium ions in the pre
Jirgensons, Aigars,Lielpetere, Anna
supporting information
(2020/07/27)
Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.
Reaction of 5'-O-protected derivatives of the anti-HIV agent stavudine (d4T) with LTMP was investigated with the aim to lithiate the vinylic hydrogens (H-3' and H-2'). When the lithiation of the 5'-O-tert-butyldiphenylsilyl derivative 5 was carried out in the presence of HMPA, an anionic silyl migration took place to give the 3'-C-silylated product 4a. The stannyl version of this reaction was found to be also possible, which has disclosed a highly simple entry to the d4T analogues variously substituted at the 3'-position by manipulating the 3'-C-stannyl d4T as a common intermediate.
Kumamoto, Hiroki,Tanaka, Hiromichi
p. 3541 - 3547
(2007/10/03)
Facile synthesis of 2',3'-unsaturated nucleosides from 2-deoxyribose
A straightforward approach for the synthesis of 2',3'-unsaturated nucleosides starting from 2-deoxyribose is described. This novel route involves two new methods; (1) preparation of 2-deoxy-1-thioribofuranoside by direct condensation of 2-deoxyribose and thiophenol, (2) formation of the nucleoside skeleton by the direct coupling of 2,3-unsaturated 1-thiopentofuranoside with pyrimidine bases.
An attempt has been made to synthesize D-ribose from D-xylose using only commercial products and a minimum number of steps. D-xylose was transformed into pentenofuranoside which then was hydrolyzed. In the pyranose series, the unsaturated derivative could
Lacourt-Gadras,Grignon-Dubois,Rezzonico
p. 281 - 288
(2007/10/02)
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