133471-17-7

Basic information

• Product Name: 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl 3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl H-phosphonate
• CAS NO: 133471-17-7
• Molecular Weight: 947.064
• Mol File: 133471-17-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl 3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl H-phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl 3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl H-phosphonate(133471-17-7)
• EPA Substance Registry System: 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl 3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl H-phosphonate(133471-17-7)

Safety Data

• Hazardous Substances Data: 133471-17-7(Hazardous Substances Data)

Upstream product

• 3868-27-7 triethylammonium 5'-O-dimethoxytritylthymidine 3'-H-phosphonate 
• 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine 
• 115244-24-1 C₅₄H₆₃N₄O₁₄PSi 

Downstream Products

• 646506-22-1 C₅₃H₇₃N₆O₁₅PSi 
• 646506-08-3 C₅₃H₇₃N₆O₁₅PSi 
• 646506-30-1 C₅₇H₇₃F₆N₈O₁₅PSi 
• 646506-31-2 C₅₈H₇₅F₆N₈O₁₅PSi 
• 646506-16-3 C₅₇H₇₃F₆N₈O₁₅PSi 
• 646506-17-4 C₅₈H₇₅F₆N₈O₁₅PSi 
• 646506-23-2 C₅₄H₇₅N₆O₁₅PSi 
• 646506-09-4 C₅₄H₇₅N₆O₁₅PSi 
• 872350-16-8 C₄₄H₄₉N₄O₁₅P 
• 872350-14-6 C₄₄H₄₉N₄O₁₅P 
• 872350-12-4 C₄₈H₆₁N₄O₁₄PSi 
• 872350-10-2 C₄₈H₆₁N₄O₁₄PSi 
• 872350-18-0 C₅₃H₆₆N₆O₁₆P₂ 
• 160343-11-3 Rp-3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl 5'-O-dimethoxytritylthymidin-3'-yl phenylphosphonate 

Relevant articles and documents

Synthesis of dinucleoside acylphosphonites by phosphonodiamidite chemistry and investigation of phosphorus epimerization

The reaction of the diamidite, (iPr2N)2PH, with acyl chlorides proceeds with the loss of HCl to give the corresponding acyl diamidites, RC(O)P(N(iPr)2)2 (R = Me (7), Ph (9)), without the intervention of sodium to give a phosphorus anion. The structure of 9 was confirmed by single-crystal X-ray diffraction. The coupling of the diamidites 7 and 9 with 5'-O-DMTr-thymidine was carried out with N-methylimidazolium triflate as the activator to give the monoamidites 3'-O-(P(N(iPr)2)C(O)R)-5'-O-DMTr-thymidine, and further coupling with 3'-O-(tert-butyldimethylsilyl)thymidine was carried out with activation by pyridinium trifluoroacetate/N-methylimidazole. The new dinucleoside acylphosphonites could be further oxidized, hydrolyzed to the H-phosphonates, and sulfurized to give the known mixture of diastereomeric phosphorothioates. The goal of this work was the measurement of the barrier to inversion of the acylphosphonites, which was expected to be low by analogy to the low barrier found in acylphosphines. However, the barrier was found to be high as no epimerization was detected up to 150 °C, and consistent with this, density functional theory calculations give an inversion barrier of over 40 kcal/mol.

Synthesis of oligodeoxyribonucleotides containing hydroxymethylphosphonate bonds in the phosphoramidite method and their hybridization properties

A set of diastereomeric TpT phosphoramidite building blocks, 1-f and 1-s, containing an alkaline-labile hydroxymethylphosphonate (HMP) linkage were synthesized. Dodecadeoxynucleotides incorporating the HMP bond were also synthesized by use of each stereoc