124424-31-3

Basic information

• Product Name: O-2,3-anhydro-1-<5-O-(monomethoxytrityl)-2-deoxy-2-fluoro-β-D-lyxofuranosyl>thymine
• Synonyms: O-2,3-anhydro-1-<5-O-(monomethoxytrityl)-2-deoxy-2-fluoro-β-D-lyxofuranosyl>thymine
• CAS NO: 124424-31-3
• Molecular Weight: 514.553
• Mol File: 124424-31-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: O-2,3-anhydro-1-<5-O-(monomethoxytrityl)-2-deoxy-2-fluoro-β-D-lyxofuranosyl>thymine(CAS DataBase Reference)
• NIST Chemistry Reference: O-2,3-anhydro-1-<5-O-(monomethoxytrityl)-2-deoxy-2-fluoro-β-D-lyxofuranosyl>thymine(124424-31-3)
• EPA Substance Registry System: O-2,3-anhydro-1-<5-O-(monomethoxytrityl)-2-deoxy-2-fluoro-β-D-lyxofuranosyl>thymine(124424-31-3)

Safety Data

• Hazardous Substances Data: 124424-31-3(Hazardous Substances Data)

Upstream product

• 124424-30-2 1-<3-O-(methylsulfonyl)-5-O-(monomethoxytrityl)-2-deoxy-2-fluoro-β-D-arabinofuranosyl>thymine 
• 127840-90-8 3-(3,5-di-O-monomethoxytrityl-β-D-arabinofuranosyl)thymine 
• 22423-26-3 O-2,2'-cyclo-5-methyluridine 
• 127840-91-9 1-(2-deoxy-2-fluoro-5-O-monomethoxytrityl-β-D-ribofuranosyl)thymine 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 69256-17-3 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 121353-88-6 1-<5-O-(monomethoxytrityl)-2-fluoro-2-deoxy-β-D-arabinofuransosyl>thymine 
• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 14470-28-1 mono-4-methoxytrityl chloride 

Downstream Products

• 124424-32-4 1-<5-O-(monomethoxytrityl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl>thymine 
• 674290-11-0 5'-O-(4-methoxytrityl)-2',3'-dideoxy-2'-fluoro-3'-acetylthioarabinothymidine 
• 127840-95-3 1-{(2R,3S,4R,5R)-3,4-Difluoro-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 127840-94-2 1-(3-azido-2-fluoro-2,3-dideoxy-β-D-ribofuranosyl)thymine 
• 124424-26-6 1-(3-azido-2,3-dideoxy-2-fluoro-β-D-arabinofuranosyl)thymine 
• 127840-92-0 1-(2-deoxy-2-fluoro-5-O-monomethoxytrityl-β-D-xylofuranosyl)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).

SYNTHESIS OF 2',3'-DISUBSTITUTED 3'-DEOXYTHYMIDINE DERIVATIVES

Reaction of 2 with DAST followed by detritylation and monomethoxytritylation afforded 34percent of the fluorinated nucleoside 3.This intermediate was used to prepare the 3'-azido-2'-fluoro- and 2',3'-difluoro substituted 5-methyluridine analogues 7 and 11, respectively.