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

Base Information

• Chemical Name: 3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)-4'-C-(2-hydroxyethyl)thymidine
• CAS No.: 221272-64-6
• Molecular Formula: C₃₉H₅₀N₂O₈Si
• Molecular Weight: 702.92
• Mol file: 221272-64-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about 3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)-4'-C-(2-hydroxyethyl)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:

benzoic 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 → 3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)-4'-C-(2-hydroxyethyl)thymidine (221272-64-6)

Guidance literature:

With potassium carbonate; In methanol; Yield given;

DOI:10.1016/S0960-894X(99)00010-4

Reference yield:

5'-O-(dimethoxytrityl)-4'-C-(2-hydroxyethyl)thymidine (203200-35-5) → 3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)-4'-C-(2-hydroxyethyl)thymidine (221272-64-6)

Guidance literature:

Multi-step reaction with 3 steps

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

2: i-Pr₂NEt / CH₂Cl₂ / 1 h / 20 °C

3: K₂CO₃ / methanol / 20 °C

With dmap; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; 1: Esterification / 2: silylation / 3: debenzylation;

DOI:10.1021/ja9934706

Reference yield:

Benzoic acid 2-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester → 3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)-4'-C-(2-hydroxyethyl)thymidine (221272-64-6)

Guidance literature:

Multi-step reaction with 2 steps

1: i-Pr₂NEt / CH₂Cl₂ / 1 h / 20 °C

2: K₂CO₃ / methanol / 20 °C

With potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; 1: silylation / 2: debenzylation;

DOI:10.1021/ja9934706

upstream raw materials:

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

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

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

tert-butyldimethylsilyl trifluoroacetate

Downstream raw materials:

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

4'-C-(2-azidoethyl)-5'-O-(dimethoxytrityl)thymidine

5'-O-(dimethoxytrityl)-4'-C-[2-(N-trifluoroacetyl)aminoethyl]thymidine

1-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(2-phenylselanyl-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione