2-cyanoethyl-N^α-(9-fluorenylmethoxycarbonyl)tyrosin-4-yl-(2',3'-di-O-acetyluridin-5'-yl)phosphate

Base Information

• Chemical Name: 2-cyanoethyl-N^α-(9-fluorenylmethoxycarbonyl)tyrosin-4-yl-(2',3'-di-O-acetyluridin-5'-yl)phosphate
• CAS No.: 537677-37-5
• Molecular Formula: C₄₀H₃₉N₄O₁₅P
• Molecular Weight: 846.741

Synonyms:2-cyanoethyl-N^α-(9-fluorenylmethoxycarbonyl)tyrosin-4-yl-(2',3'-di-O-acetyluridin-5'-yl)phosphate

Chemical Property of 2-cyanoethyl-N^α-(9-fluorenylmethoxycarbonyl)tyrosin-4-yl-(2',3'-di-O-acetyluridin-5'-yl)phosphate

Chemical Property:

Purity/Quality:

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Technology Process of 2-cyanoethyl-N^α-(9-fluorenylmethoxycarbonyl)tyrosin-4-yl-(2',3'-di-O-acetyluridin-5'-yl)phosphate

There total 10 articles about 2-cyanoethyl-N^α-(9-fluorenylmethoxycarbonyl)tyrosin-4-yl-(2',3'-di-O-acetyluridin-5'-yl)phosphate 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: 92.0%

(S)-3-(4-{(2-Cyano-ethoxy)-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester (208655-85-0) → 2-cyanoethyl-Nα-(9-fluorenylmethoxycarbonyl)tyrosin-4-yl-(2',3'-di-O-acetyluridin-5'-yl)phosphate (537677-37-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/psc.2508

Reference yield:

Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) → 2-cyanoethyl-Nα-(9-fluorenylmethoxycarbonyl)tyrosin-4-yl-(2',3'-di-O-acetyluridin-5'-yl)phosphate (537677-37-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / Cs₂CO₃ / dimethylformamide / 2 h

2: 70percent TFA / CH₂Cl₂ / 0.25 h

3: tetrazole / CH₂Cl₂; acetonitrile / 0.33 h

4: m-CPBA / CH₂Cl₂; acetonitrile / 0.33 h / 0 °C

5: HSnBu₃, AcOH / Pd(PPh₃)4 / tetrahydrofuran; CH₂Cl₂ / 1 h

With 1H-tetrazole; tri-n-butyl-tin hydride; caesium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(98)00558-9

Reference yield:

allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoate (208655-83-8) → 2-cyanoethyl-Nα-(9-fluorenylmethoxycarbonyl)tyrosin-4-yl-(2',3'-di-O-acetyluridin-5'-yl)phosphate (537677-37-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 70percent TFA / CH₂Cl₂ / 0.25 h

2: tetrazole / CH₂Cl₂; acetonitrile / 0.33 h

3: m-CPBA / CH₂Cl₂; acetonitrile / 0.33 h / 0 °C

4: HSnBu₃, AcOH / Pd(PPh₃)4 / tetrahydrofuran; CH₂Cl₂ / 1 h

With 1H-tetrazole; tri-n-butyl-tin hydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(98)00558-9

upstream raw materials:

(S)-3-(4-{(2-Cyano-ethoxy)-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester

(S)-3-(4-{(2-Cyano-ethoxy)-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (2-chloro-phenyl)-diphenyl-methyl ester

N-Fmoc-Tyr-OH

2',3'-di-O-acetyl-uridine

Downstream raw materials:

C₃₇H₄₈N₇O₂₀P

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