3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-4'-(C-iodomethyl)thymidine

Base Information

• Chemical Name: 3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-4'-(C-iodomethyl)thymidine
• CAS No.: 389873-55-6
• Molecular Formula: C₃₃H₄₇IN₂O₅Si₂
• Molecular Weight: 734.822
• Mol file: 389873-55-6.mol

Synonyms:3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-4'-(C-iodomethyl)thymidine

Chemical Property of 3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-4'-(C-iodomethyl)thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-4'-(C-iodomethyl)thymidine

There total 1 articles about 3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-4'-(C-iodomethyl)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: 85.0%

1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (162052-67-7) → 3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-4'-(C-iodomethyl)thymidine (389873-55-6)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In benzene; at 50 ℃;

DOI:10.1002/1521-3773(20011001)40:19<3693::AID-ANIE3693>3.0.CO;2-O

Reference yield:

3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-4'-(C-iodomethyl)thymidine (389873-55-6) → 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; triethylamine;

DOI:10.1002/1521-3773(20011001)40:19<3693::AID-ANIE3693>3.0.CO;2-O

Reference yield:

3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-4'-(C-iodomethyl)thymidine (389873-55-6) → 5'-O-(4,4'-dimethoxytrityl)-4'-C-(methyl)thymidine (591754-19-7)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen; Et₃N / Pd/C (10percent) / ethyl acetate; ethanol / 168 h / 20 °C

2: nBu₄NF / tetrahydrofuran / 3 h / 25 °C

3: 88 percent / pyridine; 4-(dimethylamino)pyridine / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; hydrogen; triethylamine; Pd/C (10percent); In tetrahydrofuran; ethanol; ethyl acetate;

DOI:10.1002/ejoc.200200641

upstream raw materials:

1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-4'-C-(methyl)thymidine