92127-73-6

Basic information

• Product Name: 5'-O-thymidyl 3'-O-(2'-deoxyadenosyl) phosphorothioate
• Synonyms: 5'-O-thymidyl 3'-O-(2'-deoxyadenosyl) phosphorothioate
• CAS NO: 92127-73-6
• Molecular Formula: C20H26N7O9PS
• Molecular Weight: 571.500701
• Mol File: 92127-73-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.97g/cm³
• Refractive Index: 1.837
• CAS DataBase Reference: 5'-O-thymidyl 3'-O-(2'-deoxyadenosyl) phosphorothioate(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-thymidyl 3'-O-(2'-deoxyadenosyl) phosphorothioate(92127-73-6)
• EPA Substance Registry System: 5'-O-thymidyl 3'-O-(2'-deoxyadenosyl) phosphorothioate(92127-73-6)

Safety Data

• Hazardous Substances Data: 92127-73-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H26N7O9PS/c1-9-4-26(20(31)25-19(9)30)14-2-10(29)13(35-14)6-33-37(32,38)36-11-3-15(34-12(11)5-28)27-8-24-16-17(21)22-7-23-18(16)27/h4,7-8,10-15,28-29H,2-3,5-6H2,1H3,(H,32,38)(H2,21,22,23)(H,25,30,31)/t10-,11-,12+,13+,14+,15+,37?/m0/s1

Upstream product

• 103093-86-3 C₆₉H₆₆N₇O₁₃PS₂ 
• 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine 
• 133471-14-4 (S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate 
• 118352-75-3 Triethylammonium 6-N-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)adenosine 3'-H-phosphonate 
• 115244-22-9 C₇₆H₇₀N₇O₁₄PS₂ 
• 84752-64-7 3'-O-(1,3-benzodithiol-2-yl)thymidine 
• 89947-88-6 5'-O-N⁶-di-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 
• 133471-25-7 C₅₄H₆₂N₇O₁₂PSSi 
• 103128-33-2 C₆₉H₆₆N₇O₁₃PS₃ 
• 103093-87-4 3'-adenosine 5'-thymidine phosphonate 

Relevant articles and documents

Solid-phase synthesis of stereoregular oligodeoxyribonucleoside phosphorothioates using bicyclic oxazaphospholidine derivatives as monomer units

Nucleoside 3′-O-bicylic oxazaphospholidine derivatives were designed as monomer units for a solid-phase synthesis of stereoregular oligodeoxyribonucleoside phosphorothioates (PS-ODNs). The trans-isomers of appropriately designed nucleoside 3′-O-bicyclic oxazaphospholidine derivatives were generated exclusively by the reaction between the 3′-OH of the corresponding protected nucleosides and 2-chloro-1,3,2-oxazaphospholidine derivatives. The resultant trans-oxazaphospholidine isomers were configurationally stable, and their diastereopurity was not impaired by epimerization in the presence of an acidic activator during the condensation on a solid support. As a result, the formation of both (Rp)- and (Sp)-phosphorothioate internucleotide linkages by using the oxazaphospholidine monomers and the acidic activator proceeded without any loss of diastereopurity (diastereoselectivity ≥99:1). In addition, ab initio molecular orbital calculations showed that the epimerization of oxazaphospholidine derivatives was most likely to proceed via an edge inversion process that was accelerated by N-protonation. The calculations rationalized not only the relations between the ring structure and the configurational stability of the oxazaphospholidines observed in this study but also the observations reported in the literature that the inversion of tricoordinated organophosphorus compounds were accelerated by acids or nucleophiles.

ACYLPHOSPHONATES. 7. A NEW METHOD FOR STEREOSPECIFIC AND STEREOSELECTIVE GENERATION OF DIDEOXYRIBONUCLEOSIDE PHOSPHOROTHIOATES VIA THE ACYLPHOSPHONATE INTERMEDIATES

Dideoxyribonucleoside phosphorothioates were synthesized by a new method via dideoxyribonucleoside 2,2,2-trichloroethoxycarbonylphosphonates and aroylphosphonates.The conversion of dideoxyribonucleoside 2,2,2-trichloroethoxycarbonylphosphonates to dideoxy