Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-[(9R)-11-[bis(1-methylethyl)amino]-14-cyano-9-(cyanomethyl)-7-oxo- 10,12-dioxa-2,6-diaza-11-phosphatetradecanoate]

Base Information

• Chemical Name: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-[(9R)-11-[bis(1-methylethyl)amino]-14-cyano-9-(cyanomethyl)-7-oxo- 10,12-dioxa-2,6-diaza-11-phosphatetradecanoate]
• CAS No.: 669013-14-3
• Molecular Formula: C49H62N7O11P
• Molecular Weight: 956.045

Synonyms:

Chemical Property of Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-[(9R)-11-[bis(1-methylethyl)amino]-14-cyano-9-(cyanomethyl)-7-oxo- 10,12-dioxa-2,6-diaza-11-phosphatetradecanoate]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-[(9R)-11-[bis(1-methylethyl)amino]-14-cyano-9-(cyanomethyl)-7-oxo- 10,12-dioxa-2,6-diaza-11-phosphatetradecanoate]

There total 5 articles about Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-[(9R)-11-[bis(1-methylethyl)amino]-14-cyano-9-(cyanomethyl)-7-oxo- 10,12-dioxa-2,6-diaza-11-phosphatetradecanoate] 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: 63.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + [3-((R)-4-Cyano-3-hydroxy-butyrylamino)-propyl]-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (669013-16-5) → (3-{(R)-4-Cyano-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-butyrylamino}-propyl)-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (669013-14-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2003.10.167

Reference yield:

(R)-ethyl 4-cyano-3-hydroxybutyrate (141942-85-0) → (3-{(R)-4-Cyano-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-butyrylamino}-propyl)-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (669013-14-3)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NaOH / 2 h / 20 °C

2: 64 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; aq. NaH₂PO₄ / dimethylformamide; tetrahydrofuran / 16 h / 20 °C / pH 5.7 - 6.0

3: 63 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C

With sodium hydroxide; sodium dihydrogenphosphate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2003.10.167

Reference yield:

Carbonic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 4-nitro-phenyl ester (156939-39-8) → (3-{(R)-4-Cyano-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-butyrylamino}-propyl)-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (669013-14-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / triethylamine / CH₂Cl₂ / 16 h / 20 °C

2: 64 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; aq. NaH₂PO₄ / dimethylformamide; tetrahydrofuran / 16 h / 20 °C / pH 5.7 - 6.0

3: 63 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C

With sodium dihydrogenphosphate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2003.10.167

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

[3-((R)-4-Cyano-3-hydroxy-butyrylamino)-propyl]-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

(R)-ethyl 4-cyano-3-hydroxybutyrate

Carbonic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 4-nitro-phenyl ester

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