4-{3'-deoxy-3'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-5'-deoxythymidin-5'-yl}-1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-1H-1,2,3-triazole

Base Information

Chemical Name:4-{3'-deoxy-3'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-5'-deoxythymidin-5'-yl}-1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-1H-1,2,3-triazole
CAS No.:1379761-89-3
Molecular Formula:C₅₂H₆₂N₉O₁₁P
Molecular Weight:1020.09
Hs Code.:

4-{3'-deoxy-3'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-5'-deoxythymidin-5'-yl}-1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-1H-1,2,3-triazole

Synonyms:4-{3'-deoxy-3'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-5'-deoxythymidin-5'-yl}-1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-1H-1,2,3-triazole

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Chemical Property of 4-{3'-deoxy-3'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-5'-deoxythymidin-5'-yl}-1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-1H-1,2,3-triazole

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Technology Process of 4-{3'-deoxy-3'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-5'-deoxythymidin-5'-yl}-1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-1H-1,2,3-triazole

There total 9 articles about 4-{3'-deoxy-3'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-5'-deoxythymidin-5'-yl}-1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-1H-1,2,3-triazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

: 1379761-88-2
1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-4-(5'-deoxythymidin-5'-yl)-1H-1,2,3-triazole

: 102691-36-1
N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

: 1379761-89-3
4-{3'-deoxy-3'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-5'-deoxythymidin-5'-yl}-1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-1H-1,2,3-triazole

Guidance literature:: 1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-4-(5'-deoxythymidin-5'-yl)-1H-1,2,3-triazole; With pyridine; 1H-tetrazole;

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve;
DOI:10.1002/ejoc.201101700

Reference yield: 60.0%

: 1379761-88-2
1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-4-(5'-deoxythymidin-5'-yl)-1H-1,2,3-triazole

: 124482-92-4,89992-70-1
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 1379761-89-3
4-{3'-deoxy-3'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-5'-deoxythymidin-5'-yl}-1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-1H-1,2,3-triazole

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jacs.6b11530

Reference yield:

: 151824-41-8
3'-O-tert-butyldiphenylsilyl-5'-deoxy-5'-formylthymidine

: 1379761-89-3
4-{3'-deoxy-3'-[(2-cyanoethoxy)(diisopropylamino)phosphanyloxy]-5'-deoxythymidin-5'-yl}-1-[3'-deoxy-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl]-1H-1,2,3-triazole

Guidance literature:: Multi-step reaction with 5 steps

1.1: zinc / 1,3-dioxane / 3 h / Reflux

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -70 °C

3.1: sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; copper(ll) sulfate pentahydrate / dichloromethane; water / 2 h / 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

5.1: pyridine; 1H-tetrazole

5.2: 0.5 h / 20 °C / Molecular sieve

With pyridine; 1H-tetrazole; n-butyllithium; copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; tetrabutyl ammonium fluoride; zinc; In tetrahydrofuran; 1,3-dioxane; hexane; dichloromethane; water;
DOI:10.1002/ejoc.201101700