N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxyadenosine-allyl-phosphato)-L-threonyl-L-phenylalanine methoxyethoxyethyl ester

Base Information

Chemical Name:N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxyadenosine-allyl-phosphato)-L-threonyl-L-phenylalanine methoxyethoxyethyl ester
CAS No.:197727-38-1
Molecular Formula:C₄₅H₅₆N₇O₁₅P
Molecular Weight:965.951
Hs Code.:

N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxyadenosine-allyl-phosphato)-L-threonyl-L-phenylalanine methoxyethoxyethyl ester

Synonyms:N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxyadenosine-allyl-phosphato)-L-threonyl-L-phenylalanine methoxyethoxyethyl ester

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Chemical Property of N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxyadenosine-allyl-phosphato)-L-threonyl-L-phenylalanine methoxyethoxyethyl ester

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Technology Process of N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxyadenosine-allyl-phosphato)-L-threonyl-L-phenylalanine methoxyethoxyethyl ester

There total 19 articles about N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxyadenosine-allyl-phosphato)-L-threonyl-L-phenylalanine methoxyethoxyethyl 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: 71.0%

: (S)-2-Amino-3-phenyl-propionic acid 2-(2-methoxy-ethoxy)-ethyl ester

: (2S,3R)-3-{[(2R,3S,5R)-3-Acetoxy-5-(6-amino-purin-9-yl)-tetrahydro-furan-2-ylmethoxy]-allyloxy-phosphoryloxy}-2-allyloxycarbonylamino-butyric acid

: 197727-38-1
N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxyadenosine-allyl-phosphato)-L-threonyl-L-phenylalanine methoxyethoxyethyl ester

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
DOI:10.1039/a704215i

Reference yield:

: 203986-32-7
3'-O-Acetyl-5'-O-dimethoxytrityl-6-N-phenylacetyl-2'-deoxyadenosine

: 197727-38-1
N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxyadenosine-allyl-phosphato)-L-threonyl-L-phenylalanine methoxyethoxyethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / ZnBr₂ / nitromethane / 0.25 h / Ambient temperature

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

3: t-BuOOH / CH₂Cl₂ / 0.17 h / 0 °C

4: 70 percent / papain, L-cysteine, phosphate buffer (pH 6.6) / acetone / 37 °C

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

With 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:

: 155501-21-6
3'-O-Acetyl-6-N-phenylacetyl-2'-deoxyadenosine

: 197727-38-1
N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxyadenosine-allyl-phosphato)-L-threonyl-L-phenylalanine methoxyethoxyethyl ester

Guidance literature:: Multi-step reaction with 4 steps

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

2: t-BuOOH / CH₂Cl₂ / 0.17 h / 0 °C

3: 70 percent / papain, L-cysteine, phosphate buffer (pH 6.6) / acetone / 37 °C

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

With 1H-tetrazole; tert.-butylhydroperoxide; phosphate buffer; L-Cysteine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; papain; In dichloromethane; acetone; acetonitrile;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<669::AID-CHEM669>3.0.CO;2-V