1-(3-O-(2-cyanoethoxy(diisopropylamino)phosphino)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine

Base Information

• Chemical Name: 1-(3-O-(2-cyanoethoxy(diisopropylamino)phosphino)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine
• CAS No.: 1331770-53-6
• Molecular Formula: C₄₀H₄₈FN₄O₈P
• Molecular Weight: 762.815

Synonyms:1-(3-O-(2-cyanoethoxy(diisopropylamino)phosphino)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine

Chemical Property of 1-(3-O-(2-cyanoethoxy(diisopropylamino)phosphino)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine

Chemical Property:

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Technology Process of 1-(3-O-(2-cyanoethoxy(diisopropylamino)phosphino)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine

There total 5 articles about 1-(3-O-(2-cyanoethoxy(diisopropylamino)phosphino)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine 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: 94.0%

1-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine (1331770-51-4,133324-02-4) + N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) → 1-(3-O-(2-cyanoethoxy(diisopropylamino)phosphino)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine (1331770-53-6)

Guidance literature:

With N,N-diisopropylamine tetrazolide; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1002/cbic.201100161

Reference yield:

C23H26O7 (1331770-45-6) → 1-(3-O-(2-cyanoethoxy(diisopropylamino)phosphino)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine (1331770-53-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.75 h / Reflux

1.2: 25 h / 80 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

3.1: ammonia / methanol; dichloromethane / 4 h / 20 °C

4.1: pyridine; (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 20 h / 20 °C

5.1: boron trichloride / dichloromethane / 0.5 h / -78 °C

5.2: 22 h / 20 °C

6.1: pyridine / 3 h / 20 °C

7.1: N,N-diisopropylamine tetrazolide / dichloromethane / 18 h / 20 °C / Inert atmosphere

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; N,N-diisopropylamine tetrazolide; ammonia; boron trichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/cbic.201100161

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → 1-(3-O-(2-cyanoethoxy(diisopropylamino)phosphino)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine (1331770-53-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.75 h / Reflux

1.2: 25 h / 80 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

3.1: ammonia / methanol; dichloromethane / 4 h / 20 °C

4.1: pyridine; (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 20 h / 20 °C

5.1: boron trichloride / dichloromethane / 0.5 h / -78 °C

5.2: 22 h / 20 °C

6.1: pyridine / 3 h / 20 °C

7.1: N,N-diisopropylamine tetrazolide / dichloromethane / 18 h / 20 °C / Inert atmosphere

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; N,N-diisopropylamine tetrazolide; ammonia; boron trichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/cbic.201100161

upstream raw materials:

1-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-α-L-ribofuranosyl)thymine

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

C₂₃H₂₆O₇

1-(2-O-acetyl-3,5-di-O-benzyl-α-L-arabinofuranosyl)thymine

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