183075-04-9Relevant academic research and scientific papers
Facile synthesis of 2',3'-unsaturated nucleosides from 2-deoxyribose
Sujino, Keiko,Yoshida, Tomoyasu,Sugimura, Hideyuki
, p. 6133 - 6136 (1996)
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.
Electrophilic glycosidation employing 3,5-O-(di-tert-butylsilylene)-erythro-furanoid glycal leads to exclusive formation of the β-anomer: synthesis of 2′-deoxynucleosides and its 1′-branched analogues
Haraguchi, Kazuhiro,Konno, Kiju,Yamada, Kaori,Kitagawa, Yasuyuki,Nakamura, Kazuo T.,Tanaka, Hiromichi
scheme or table, p. 4587 - 4600 (2010/07/05)
Stereoselectivity in N-iodosuccimide (NIS)-mediated electrophilic glycosidation was examined by employing 2,4-bis-O-(trimethylsilyl)thymine and three different silyl-protected erythro-furanoid glycals 12, 16, and 18. As a result, it was found that 3,5-O-(di-t-butylsilylene)-protected 18 gave only the β-anomer (21). The remarkable stereoselectivity observed by employing 18 is discussed on the basis of its X-ray crystallographic analysis. 1-Substituted glycals gave the corresponding β-anomer, again exclusively, to provide access to 1′-branched 2′-deoxynucleosides.
