Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-[P-[2-(2-cyano-1,1-dimethylethoxy)-2-oxoethyl]-N,N-bis(1-methylethyl) phosphonamidite]

Base Information

• Chemical Name: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-[P-[2-(2-cyano-1,1-dimethylethoxy)-2-oxoethyl]-N,N-bis(1-methylethyl) phosphonamidite]
• CAS No.: 411234-18-9
• Molecular Formula: C44H55N4O9P
• Molecular Weight: 814.916
• Mol file: 411234-18-9.mol

Synonyms:

Chemical Property of Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-[P-[2-(2-cyano-1,1-dimethylethoxy)-2-oxoethyl]-N,N-bis(1-methylethyl) phosphonamidite]

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Technology Process of Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-[P-[2-(2-cyano-1,1-dimethylethoxy)-2-oxoethyl]-N,N-bis(1-methylethyl) phosphonamidite]

There total 3 articles about Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-[P-[2-(2-cyano-1,1-dimethylethoxy)-2-oxoethyl]-N,N-bis(1-methylethyl) phosphonamidite] 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: 86.0%

5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) + acetic acid, [bis(N,N-diisopropylamino)phosphino]-1,1-dimethyl-2-cyanoethyl ester (411234-03-2) → 3'-O-(diisopropylamino)phosphinoacetic acid α,α-dimethyl-β-cyanoethyl ester 5'-O-(4,4'-dimethoxytrityl)thymidine (411234-18-9)

Guidance literature:

With 1H-tetrazole; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1021/ja027983f

Reference yield:

3-hydroxy-3-methylbutyronitrile (13635-04-6) → 3'-O-(diisopropylamino)phosphinoacetic acid α,α-dimethyl-β-cyanoethyl ester 5'-O-(4,4'-dimethoxytrityl)thymidine (411234-18-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / toluene / Heating

2: 88 percent / Zn / tetrahydrofuran; diethyl ether / 0.5 h / Heating

3: 86 percent / tetrazole / CH₂Cl₂ / 48 h / 20 °C

With 1H-tetrazole; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2: Reformatsky reaction;

DOI:10.1021/ja027983f

Reference yield:

1-cyano-2-methylpropan-2-yl 2-bromoacetate (411234-02-1) → 3'-O-(diisopropylamino)phosphinoacetic acid α,α-dimethyl-β-cyanoethyl ester 5'-O-(4,4'-dimethoxytrityl)thymidine (411234-18-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / Zn / tetrahydrofuran; diethyl ether / 0.5 h / Heating

2: 86 percent / tetrazole / CH₂Cl₂ / 48 h / 20 °C

With 1H-tetrazole; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Reformatsky reaction;

DOI:10.1021/ja027983f

upstream raw materials:

5'-O-(4-4'-dimethoxytrityl)thymidine

acetic acid, [bis(N,N-diisopropylamino)phosphino]-1,1-dimethyl-2-cyanoethyl ester

3-hydroxy-3-methylbutyronitrile

1-cyano-2-methylpropan-2-yl 2-bromoacetate

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