N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid γ-allyl ester-methoxyethyl ester

Base Information

• Chemical Name: N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid γ-allyl ester-methoxyethyl ester
• CAS No.: 221351-11-7
• Molecular Formula: C₄₀H₅₂N₅O₁₇P
• Molecular Weight: 905.85

Synonyms:N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid γ-allyl ester-methoxyethyl ester

Chemical Property of N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid γ-allyl ester-methoxyethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid γ-allyl ester-methoxyethyl ester

There total 12 articles about N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid γ-allyl ester-methoxyethyl 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:

4-Amino-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one (51432-42-9) → N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid γ-allyl ester-methoxyethyl ester (221351-11-7)

Guidance literature:

Multi-step reaction with 9 steps

1: HOBt, pyridine / acetonitrile / 12 h

2: NH₃, H₂O

3: 96 percent / pyridine / 3 h / Ambient temperature

4: 84 percent / pyridine / 4 h

5: 92 percent / ZnBr₂ / nitromethane / 0.25 h / Ambient temperature

6: tetrazole / CH₂Cl₂; acetonitrile / 18 h / Ambient temperature

7: tBuOOH / CH₂Cl₂ / 0.17 h / 0 °C

8: 91 percent / papain, L-cysteine, phosphate buffer (pH 6.6) / acetone / 37 °C

9: 1.) HOBt, EDC, 2.) diisopropylethylamine / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, r.t., 15 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; phosphate buffer; L-Cysteine; ammonia; water; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; zinc dibromide; papain; In nitromethane; dichloromethane; acetone; acetonitrile;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<669::AID-CHEM669>3.0.CO;2-V

Reference yield:

4-N-Phenylacetyl-2'-deoxycytidine (173978-68-2) → N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid γ-allyl ester-methoxyethyl ester (221351-11-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / pyridine / 3 h / Ambient temperature

2: 84 percent / pyridine / 4 h

3: 92 percent / ZnBr₂ / nitromethane / 0.25 h / Ambient temperature

4: tetrazole / CH₂Cl₂; acetonitrile / 18 h / Ambient temperature

5: tBuOOH / CH₂Cl₂ / 0.17 h / 0 °C

6: 91 percent / papain, L-cysteine, phosphate buffer (pH 6.6) / acetone / 37 °C

7: 1.) HOBt, EDC, 2.) diisopropylethylamine / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, r.t., 15 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; phosphate buffer; L-Cysteine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; zinc dibromide; papain; In nitromethane; dichloromethane; acetone; acetonitrile;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<669::AID-CHEM669>3.0.CO;2-V

Reference yield:

5'-O-Dimethoxytrityl-4-N-phenylacetyl-2'-deoxycytidine (190192-16-6) → N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid γ-allyl ester-methoxyethyl ester (221351-11-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / pyridine / 4 h

2: 92 percent / ZnBr₂ / nitromethane / 0.25 h / Ambient temperature

3: tetrazole / CH₂Cl₂; acetonitrile / 18 h / Ambient temperature

4: tBuOOH / CH₂Cl₂ / 0.17 h / 0 °C

5: 91 percent / papain, L-cysteine, phosphate buffer (pH 6.6) / acetone / 37 °C

6: 1.) HOBt, EDC, 2.) diisopropylethylamine / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, r.t., 15 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; phosphate buffer; L-Cysteine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; zinc dibromide; papain; In nitromethane; dichloromethane; acetone; acetonitrile;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<669::AID-CHEM669>3.0.CO;2-V

upstream raw materials:

N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-serine

4-Amino-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

4-N-Phenylacetyl-2'-deoxycytidine

5'-O-Dimethoxytrityl-4-N-phenylacetyl-2'-deoxycytidine

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