4'-Vinyl-5'-O-(4,4'-dimethoxytrityl)thymidine

Base Information

• Chemical Name: 4'-Vinyl-5'-O-(4,4'-dimethoxytrityl)thymidine
• CAS No.: 246022-21-9
• Molecular Formula: C₃₃H₃₄N₂O₇
• Molecular Weight: 570.642
• DSSTox Substance ID: DTXSID201169974
• Nikkaji Number: J1.217.039D
• Mol file: 246022-21-9.mol

Synonyms:DTXSID201169974;4'-Vinyl-5'-O-(4,4'-dimethoxytrityl)thymidine;Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-4'-C-ethenyl-;246022-21-9

Chemical Property of 4'-Vinyl-5'-O-(4,4'-dimethoxytrityl)thymidine

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 570.23660143
• Heavy Atom Count: 42
• Complexity: 970

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)(COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)C=C)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@](O2)(COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)C=C)O

Technology Process of 4'-Vinyl-5'-O-(4,4'-dimethoxytrityl)thymidine

There total 9 articles about 4'-Vinyl-5'-O-(4,4'-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: 61.0%

1-[5-O-(4,4'-dimethoxytrityl)-3-O-diphenylvinylsilyl-4-C-phenylseleno-2-deoxy-α-L-erythro-pento-1,4-furanosyl]thymine → 5'-O-(4,4'-dimethoxytrityl)-4'αC-vinylthymidine (246022-21-9)

Guidance literature:

1-[5-O-(4,4'-dimethoxytrityl)-3-O-diphenylvinylsilyl-4-C-phenylseleno-2-deoxy-α-L-erythro-pento-1,4-furanosyl]thymine; With bis(tri-n-butyltin); In benzene; at 20 ℃; UV-irradiation;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; benzene; at 20 ℃;

DOI:10.1021/jo990787f

Reference yield:

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 (203200-32-2) → 5'-O-(4,4'-dimethoxytrityl)-4'αC-vinylthymidine (246022-21-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: (Bu₃Sn)2 / benzene / 20 °C / UV-irradiation

2.2: 61 percent / TBAF / tetrahydrofuran; benzene / 20 °C

With dmap; bis(tri-n-butyltin); triethylamine; In toluene; benzene; 1.1: Substitution / 2.1: Cyclization / 2.2: Ring cleavage;

DOI:10.1021/jo990787f

Reference yield:

1-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione → 5'-O-(4,4'-dimethoxytrityl)-4'αC-vinylthymidine (246022-21-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

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

upstream raw materials:

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

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

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