3'-deoxy-3'-C-[[(2-cyanoethoxy)phosphinyl]methyl]-5'-O-(4-methoxytrityl)thymidine

Base Information

Chemical Name:3'-deoxy-3'-C-[[(2-cyanoethoxy)phosphinyl]methyl]-5'-O-(4-methoxytrityl)thymidine
CAS No.:337980-13-9
Molecular Formula:C₃₄H₃₆N₃O₇P
Molecular Weight:629.649
Hs Code.:

Synonyms:3'-deoxy-3'-C-[[(2-cyanoethoxy)phosphinyl]methyl]-5'-O-(4-methoxytrityl)thymidine

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Chemical Property of 3'-deoxy-3'-C-[[(2-cyanoethoxy)phosphinyl]methyl]-5'-O-(4-methoxytrityl)thymidine

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Technology Process of 3'-deoxy-3'-C-[[(2-cyanoethoxy)phosphinyl]methyl]-5'-O-(4-methoxytrityl)thymidine

There total 7 articles about 3'-deoxy-3'-C-[[(2-cyanoethoxy)phosphinyl]methyl]-5'-O-(4-methoxytrityl)thymidine 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: 79.0%

: 109-78-4
3-Hydroxypropionitrile

: 3'-deoxy-3'-C-[(hydroxyphosphinyl)methyl]-5'-O-(4-methoxytrityl)thymidine triethylamine salt

: 337980-13-9
3'-deoxy-3'-C-[[(2-cyanoethoxy)phosphinyl]methyl]-5'-O-(4-methoxytrityl)thymidine

Guidance literature:: With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 65 ℃; for 24h;
DOI:10.1021/jo001699u

Reference yield:

: 146557-69-9
1-[5-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-(formyl)-β-D-erythro-pentofuranosyl]thymine

: 337980-13-9
3'-deoxy-3'-C-[[(2-cyanoethoxy)phosphinyl]methyl]-5'-O-(4-methoxytrityl)thymidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 3.99 g / NaBH₄ / ethanol; H₂O / 2 h / 20 °C

2.1: 85 percent / methyl triphenoxyphosphonium iodide; 2,6-lutidine / dimethylformamide / 0 - 20 °C

3.1: 94 percent / triethylamine trifluoride / tetrahydrofuran / 20 °C

4.1: 84.3 percent / diisopropylethylamine / ethyl acetate; tetrahydrofuran / 20 °C

5.1: bis(trimethylsilyl)phosphonite; diisopropylethylamine / CH₂Cl₂ / 20 °C

5.2: 36 percent / MeOH / tetrahydrofuran / 20 °C

6.1: 79 percent / DCC / tetrahydrofuran / 24 h / 65 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; bis(trimethylsilyl) phosphonate; triethylamine trifluoride; methyltriphenoxyphosphonium iodide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 5.1: Arbuzov reaction;
DOI:10.1021/jo001699u

Reference yield:

: 146557-80-4
1-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}thymine

: 337980-13-9
3'-deoxy-3'-C-[[(2-cyanoethoxy)phosphinyl]methyl]-5'-O-(4-methoxytrityl)thymidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 85 percent / methyl triphenoxyphosphonium iodide; 2,6-lutidine / dimethylformamide / 0 - 20 °C

2.1: 94 percent / triethylamine trifluoride / tetrahydrofuran / 20 °C

3.1: 84.3 percent / diisopropylethylamine / ethyl acetate; tetrahydrofuran / 20 °C

4.1: bis(trimethylsilyl)phosphonite; diisopropylethylamine / CH₂Cl₂ / 20 °C

4.2: 36 percent / MeOH / tetrahydrofuran / 20 °C

5.1: 79 percent / DCC / tetrahydrofuran / 24 h / 65 °C

With 2,6-dimethylpyridine; bis(trimethylsilyl) phosphonate; triethylamine trifluoride; methyltriphenoxyphosphonium iodide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 4.1: Arbuzov reaction;
DOI:10.1021/jo001699u