4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine

Base Information

Chemical Name:4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine
CAS No.:267243-98-1
Molecular Formula:C₃₉H₄₉N₅O₇Si
Molecular Weight:727.933
Hs Code.:

Synonyms:4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine

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Chemical Property of 4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine

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Technology Process of 4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine

There total 7 articles about 4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)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:

: methanesulfonic acid 2-[2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

: 267243-98-1
4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/ja9934706

Reference yield:

: 203200-35-5
5'-O-(dimethoxytrityl)-4'-C-(2-hydroxyethyl)thymidine

: 267243-98-1
4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N; DMAP / CH₂Cl₂ / 0.17 h / -78 °C

2: i-Pr₂NEt / CH₂Cl₂ / 1 h / 20 °C

3: K₂CO₃ / methanol / 20 °C

4: Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

5: NaN₃ / dimethylformamide / 20 °C

With dmap; sodium azide; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: silylation / 3: debenzylation / 4: mesylation / 5: Substitution;
DOI:10.1021/ja9934706

Reference yield:

: 203200-33-3
1-[3-O-(vinyldimethylsilyl)-2-deoxy-5-O-(dimethoxytrityl)-4-C-(phenylseleno)-α-L-threo-pento-1,4-furanosyl]thymine

: 267243-98-1
4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: Bu₃SnH; AIBN / benzene / 80 °C

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

2.1: Et₃N; DMAP / CH₂Cl₂ / 0.17 h / -78 °C

3.1: i-Pr₂NEt / CH₂Cl₂ / 1 h / 20 °C

4.1: K₂CO₃ / methanol / 20 °C

5.1: Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

6.1: NaN₃ / dimethylformamide / 20 °C

With dmap; sodium azide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In 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;
DOI:10.1021/ja9934706