674290-11-0

Basic information

• Product Name: 5'-O-(4-methoxytrityl)-2',3'-dideoxy-2'-fluoro-3'-acetylthioarabinothymidine
• Synonyms: 5'-O-(4-methoxytrityl)-2',3'-dideoxy-2'-fluoro-3'-acetylthioarabinothymidine
• CAS NO: 674290-11-0
• Molecular Weight: 590.672
• Mol File: 674290-11-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5'-O-(4-methoxytrityl)-2',3'-dideoxy-2'-fluoro-3'-acetylthioarabinothymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4-methoxytrityl)-2',3'-dideoxy-2'-fluoro-3'-acetylthioarabinothymidine(674290-11-0)
• EPA Substance Registry System: 5'-O-(4-methoxytrityl)-2',3'-dideoxy-2'-fluoro-3'-acetylthioarabinothymidine(674290-11-0)

Safety Data

• Hazardous Substances Data: 674290-11-0(Hazardous Substances Data)

Upstream product

• 34832-35-4 sodium thioacetate 
• 124424-31-3 O-2,3-anhydro-1-<5-O-(monomethoxytrityl)-2-deoxy-2-fluoro-β-D-lyxofuranosyl>thymine 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 69256-17-3 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine 

Relevant articles and documents

Synthesis of 2',3'-dideoxy-2'-fluoro-3'-thioarabinothymidine and its 3'-phosphoramidite derivative.

An efficient method for the synthesis of 5'-O-monomethoxytrityl-2',3'-dideoxy-2'-fluoro-3'-thioarabinothymidine [(5'MMT)araF-T(3'SH), (5)] and its 3'-phosphoramidite derivative (6) suitable for automated incorporation into oligonucleotides, is demonstrated. A key step in the synthesis involves reaction of 5'-O-MMT-2,3'-O-anhydrothymidine (4) (Eleuteri, A.; Reese, C.B.; Song, Q. J. Chem. Soc. Perkin Trans. 1 1996, 2237 pp.) with sodium thioacetate to give (5'-MMT)araF-T(3'SAc) (5) (Elzagheid, M.I.; Mattila, K.; Oivanen, M.; Jones, B.C.N.M.; Cosstick, Loennberg, H. Eur. J. Org. Chem. 2000, 1987-1991). This nucleoside was then converted to its corresponding phosphoramidite derivative, 6, as described previously ((a) Sun, S.; Yoshida, A.; Piccirilli, J.A. RNA, 1997, 3, 1352-1363; (b) Matulic-Adamic, J.; Beigelman, L. Helvetica Chemica Acta 1999, 82, 2141-2150: (c) Fettes, K.J.; O'Neil, I.; Roberts, S.M.; Cosstick, R. Nucleosides, Nucleotides and Nucl. Acids 2001, 20, 1351-1354).