5'-O-(dimethoxytrityl)-4'-C-[3-(N-trifluoroacetyl)aminopropyl]thymidine

Base Information

Chemical Name:5'-O-(dimethoxytrityl)-4'-C-[3-(N-trifluoroacetyl)aminopropyl]thymidine
CAS No.:267244-05-3
Molecular Formula:C₃₆H₃₈F₃N₃O₈
Molecular Weight:697.708
Hs Code.:

Synonyms:5'-O-(dimethoxytrityl)-4'-C-[3-(N-trifluoroacetyl)aminopropyl]thymidine

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Chemical Property of 5'-O-(dimethoxytrityl)-4'-C-[3-(N-trifluoroacetyl)aminopropyl]thymidine

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Technology Process of 5'-O-(dimethoxytrityl)-4'-C-[3-(N-trifluoroacetyl)aminopropyl]thymidine

There total 10 articles about 5'-O-(dimethoxytrityl)-4'-C-[3-(N-trifluoroacetyl)aminopropyl]thymidine 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:

: 203200-32-2
1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-5-phenylselanyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

: 267244-05-3
5'-O-(dimethoxytrityl)-4'-C-[3-(N-trifluoroacetyl)aminopropyl]thymidine

Guidance literature:: Multi-step reaction with 10 steps

1.1: 92 percent / DMAP; Et₃N / toluene / 0.5 h / 20 °C

2.1: Bu₃SnH; AIBN / benzene / 80 °C

2.2: 66 percent / 30percent aq. H₂O₂; KF; KHCO₃ / methanol; tetrahydrofuran / 20 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / -78 - 0 °C

4.1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

5.1: K₂CO₃ / methanol / 20 °C

6.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

7.1: NaN₃ / dimethylformamide / 20 °C

8.1: 86 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

9.1: H₂ / 10percent Pd/C / methanol / 20 °C / 760.05 Torr

10.1: Et₃N / methanol / 2 h / 20 °C

With dmap; sodium azide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1.1: silylation / 2.1: radical rearrangement / 2.2: Tamao oxidation / 3.1: Esterification / 4.1: silylation / 5.1: debenzylation / 6.1: mesylation / 7.1: Substitution / 8.1: desilylation / 9.1: catalytic reduction / 10.1: Acylation;
DOI:10.1021/ja9934706

Reference yield:

: 267243-96-9
5'-O-(dimethoxytrityl)-4'-C-(3-hydroxypropyl)thymidine

: 267244-05-3
5'-O-(dimethoxytrityl)-4'-C-[3-(N-trifluoroacetyl)aminopropyl]thymidine

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N; DMAP / CH₂Cl₂ / 2 h / -78 - 0 °C

2: i-Pr₂NEt / CH₂Cl₂ / 20 °C

3: K₂CO₃ / methanol / 20 °C

4: Et₃N / CH₂Cl₂ / 2 h / 20 °C

5: NaN₃ / dimethylformamide / 20 °C

6: 86 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

7: H₂ / 10percent Pd/C / methanol / 20 °C / 760.05 Torr

8: Et₃N / methanol / 2 h / 20 °C

With dmap; sodium azide; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: silylation / 3: debenzylation / 4: mesylation / 5: Substitution / 6: desilylation / 7: catalytic reduction / 8: Acylation;
DOI:10.1021/ja9934706

Reference yield:

: 267243-95-8
1-[3-O-(allyldimethylsilyl)-2-deoxy-5-O-(dimethoxytrityl)-4-C-(phenylseleno)-α-L-threo-pento-1,4-furanosyl]thymine

: 267244-05-3
5'-O-(dimethoxytrityl)-4'-C-[3-(N-trifluoroacetyl)aminopropyl]thymidine

Guidance literature:: Multi-step reaction with 9 steps

1.1: Bu₃SnH; AIBN / benzene / 80 °C

1.2: 66 percent / 30percent aq. H₂O₂; KF; KHCO₃ / methanol; tetrahydrofuran / 20 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / -78 - 0 °C

3.1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

4.1: K₂CO₃ / methanol / 20 °C

5.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

6.1: NaN₃ / dimethylformamide / 20 °C

7.1: 86 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

8.1: H₂ / 10percent Pd/C / methanol / 20 °C / 760.05 Torr

9.1: Et₃N / methanol / 2 h / 20 °C

With dmap; sodium azide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: radical rearrangement / 1.2: Tamao oxidation / 2.1: Esterification / 3.1: silylation / 4.1: debenzylation / 5.1: mesylation / 6.1: Substitution / 7.1: desilylation / 8.1: catalytic reduction / 9.1: Acylation;
DOI:10.1021/ja9934706