(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

Base Information

• Chemical Name: (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
• CAS No.: 208655-85-0
• Molecular Formula: C₄₃H₄₃N₄O₁₅P
• Molecular Weight: 886.806
• Mol file: 208655-85-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 5 articles about (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 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: 90.0%

(S)-allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-hydroxyphenyl)propanoate (143674-78-6) + 2',3'-di-O-acetyluridine-5'-O-yl(2-cyanoethoxy)(diisopropylamino)phosphane (208655-84-9) → (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)

Guidance literature:

(S)-allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-hydroxyphenyl)propanoate; 2',3'-di-O-acetyluridine-5'-O-yl(2-cyanoethoxy)(diisopropylamino)phosphane; With 4,5-dicyano-1H-imidazole; In acetonitrile; at 20 ℃; for 0.5h;

With tert.-butylhydroperoxide; In acetonitrile; at 20 ℃; for 0.75h;

DOI:10.1002/psc.2508

Reference yield:

(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]-phosphanyloxy}-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 allyl ester (208655-85-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile; at 0 ℃; for 0.333333h;

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

Reference yield:

Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) → (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)

Guidance literature:

Multi-step reaction with 4 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

With 1H-tetrazole; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

Fmoc-Tyr(tBu)-OH

(S)-allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-hydroxyphenyl)propanoate

allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoate

2',3'-di-O-acetyluridine-5'-O-yl(2-cyanoethoxy)(diisopropylamino)phosphane

Downstream raw materials:

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

C₃₇H₄₈N₇O₂₀P