104655-76-7

Basic information

• Product Name: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-(tetraethylphosphorodiamidite)
• CAS NO: 104655-76-7
• Molecular Formula: C39H51N4O7P
• Molecular Weight: 718.83
• Mol File: 104655-76-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-(tetraethylphosphorodiamidite)(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-(tetraethylphosphorodiamidite)(104655-76-7)
• EPA Substance Registry System: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-(tetraethylphosphorodiamidite)(104655-76-7)

Safety Data

• Hazardous Substances Data: 104655-76-7(Hazardous Substances Data)

Upstream product

• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 2283-11-6 hexaethylphosphoric triamide 
• 685-83-6 bis(diethylamino)chlorophosphine 

Downstream Products

• 340026-90-6 5'-O-(4,4'-dimethoxytrityl)-3'-O-(N,N-diethylamino)[3-(N-methylaminocarbonyl)-1-propyloxy]phosphinyl-2'-deoxythymidine 
• 50571-26-1 5'-O-dimethoxytritylthymidine 3'-H-phosphonate 
• 340026-91-7 5'-O-(4,4'-dimethoxytrityl)-3'-O-(N,N-diethylamino)[3-(N-tert-butylaminocarbonyl)-1-propyloxy]phosphinylthymidine 
• 471878-68-9 5'-O-(4,4'-dimethoxytrityl)-3'-O-(N,N-diethylamino)[(N-tert-butylaminocarbonyl)methyloxy]phosphinylthymidine 
• 127105-12-8 O-(5'-O-dimethoxytritylthymidin-3'-yl) S-(2-cyanoethyl) N,N-diethylthiophosphoramidite 

Relevant articles and documents

The 3-(N-tert-butylcarboxamido)-1-propyl group as an attractive phosphate/thiophosphate protecting group for solid-phase oligodeoxyribonucleotide synthesis

Among the various phosphate/thiophosphate protecting groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-propyl group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t1/2 ～ 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate group as a 2-(tertbutylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-propyl group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 °C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-propyl group represents an attractive alternative to the 2-cyanoethyl group toward the large-scale preparation of therapeutic oligonucleotides.

Deoxyribonucleoside Phosphorodithioates. Preparation of Dinucleoside Phosphorodithioates from Nucleoside Thiophosphoramidites

A series of protected thymidine thiophosphoramidites have been prepared and their properties evaluated.Although less reactive than phosphoramidites, thiophosphoramidites with small N-substituents (methyl) are useful synthons for the preparation of nucleoside phosphorodithioates, as demonstrated by the preparation of a thymidine dimer.The coupling reactions are not as clean as those of the analogous phosphoramidites since the alkylthio group is somewhat labile.