202719-47-9

Upstream product

• 5983-15-3 O^3'-acetyl-5'-oxo-5'-deoxy-thymidine 
• 155193-99-0 5'-{3-[(3'R)-5'-(4,4'-Dimethoxytrityl)-3'-deoxythymidin-3'-yl]-2-oxopropyl}-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-deoxythymidine 
• 202719-44-6 3'-O-Acetyl-5'-{3-[(3'R)-5'-(4,4'-dimethoxytrityl)-3'-deoxythymidin-3'-yl]-2-oxopropyl}-5'-deoxythymidine 
• 202719-45-7 5'-{3-[(3'R)-5'-(4,4'-Dimethoxytrityl)-3'-deoxythymidin-3'-yl]-2-oxopropyl}-5'-deoxythymidine 
• 202719-30-0 (E)-3'-O-Acetyl-5'-(3-{(3'R)-5'-O-(tert-butyldimethylsilyl)-3-[(2-trimethylsilylethoxy)methyl]-3'-deoxythymidin-3'-yl}-2-oxopropylidene)-5'-deoxythymidine 
• 202719-38-8 (E)-3'-O-Acetyl-5'-{3-[(3'R)-3-benzyloxymethyl-5'-O-(tert-butyldimethylsilyl)-3'-deoxythymidin-3'-yl]-2-oxopropylidene}-5'-deoxythymidine 
• 202719-31-1 C₃₁H₄₆N₄O₁₁Si 
• 202719-37-7 3-Benzyloxymethyl-1-{(2R,4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 202719-28-6 1-{(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-5-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrimidine-2,4-dione 
• 202719-32-2 3'-O-Acetyl-5'-[3-((3'R)-3'-deoxythymidin-3'-yl)-2-oxopropyl]-5'-deoxythymidine 
• 202724-78-5 3-Benzyloxymethyl-1-[(2R,4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-(2-imidazol-1-yl-2-oxo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 202724-76-3 1-[(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-imidazol-1-yl-2-oxo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrimidine-2,4-dione 
• 202719-35-5 [(2S,3R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-acetic acid 
• 202719-25-3 {(2S,3R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-[5-methyl-2,4-dioxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl}-acetic acid 

Relevant academic research and scientific papers

Synthesis of analogues of oligonucleotides; synthesis of unprotected C-linked di- and tri-nucleotides

The Wittig reaction between the N-benzyloxymethylthymidine-derived ylide 25 and the aldehyde 16 followed by hydrogenolysis gives access to the unprotected C-linked dinucleotide 20 on a multi-gram scale. Oxidation of the dinucleotide gives the aldehyde 27 which is condensed with the ylide 25 to give the unprotected bis-C-linked trinucleotide 29 after hydrogenolysis. The mono-C-linked trinucleotide 44 is prepared by oxidation of the dinucleotide ester 34 to the aldehyde 36 which is condensed with the ylide 25 followed by hydrogenolysis to give the mono-C-linked trinucleotide ester 38. This intermediate is also prepared from the C-linked dinucleotide 20 by conversion into the phosphoramidite 41 which is coupled with 3-acetylthymidine 15 to give the mono-C-linked trinucleotide phosphite 42. Oxidation and deprotection give the phosphate triester 38. Treatment of 38 with methanolic ammonia gives the fully unprotected mono-C-linked trinucleotide 44.