Thymidine, 5'-O-[(1,1-dimethylethyl)diphenylsilyl]-3'-O-[(2S,5S)-3-methyl-5-phenyl-1, 3,2-oxazaphospholidin-2-yl]-

Base Information

• Chemical Name: Thymidine, 5'-O-[(1,1-dimethylethyl)diphenylsilyl]-3'-O-[(2S,5S)-3-methyl-5-phenyl-1, 3,2-oxazaphospholidin-2-yl]-
• CAS No.: 434937-14-1
• Molecular Formula: C35H42N3O6PSi
• Molecular Weight: 659.794
• Mol file: 434937-14-1.mol

Synonyms:

Chemical Property of Thymidine, 5'-O-[(1,1-dimethylethyl)diphenylsilyl]-3'-O-[(2S,5S)-3-methyl-5-phenyl-1, 3,2-oxazaphospholidin-2-yl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thymidine, 5'-O-[(1,1-dimethylethyl)diphenylsilyl]-3'-O-[(2S,5S)-3-methyl-5-phenyl-1, 3,2-oxazaphospholidin-2-yl]-

There total 2 articles about Thymidine, 5'-O-[(1,1-dimethylethyl)diphenylsilyl]-3'-O-[(2S,5S)-3-methyl-5-phenyl-1, 3,2-oxazaphospholidin-2-yl]- 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:

5'-O-tert-butyldiphenylsilylthymidine (101527-40-6) + (5S)-2-chloro-3-methyl-5-phenyl-1,3,2-oxazaphospholidine (573987-70-9) → 5'-O-(tert-butyldiphenylsilyl)-3'-O-[(2S,5S)-3-methyl-5-phenyl-1,3,2-oxazaphospholidin-2-yl]thymidine (434937-14-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ja034502z

Reference yield:

N-methyl (S)-2-hydroxy-2-phenylethylamine (65058-52-8,6589-55-5) → 5'-O-(tert-butyldiphenylsilyl)-3'-O-[(2S,5S)-3-methyl-5-phenyl-1,3,2-oxazaphospholidin-2-yl]thymidine (434937-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1: PCl₃; N-methylmorpholine / toluene / 0 - 20 °C

2: 772 mg / Et₃N / tetrahydrofuran / -78 - 20 °C

With 4-methyl-morpholine; triethylamine; phosphorus trichloride; In tetrahydrofuran; toluene;

DOI:10.1021/ja034502z

Reference yield:

3'-O-(t-butyldimethylsilyl)thymidine (40733-27-5) + 5'-O-(tert-butyldiphenylsilyl)-3'-O-[(2S,5S)-3-methyl-5-phenyl-1,3,2-oxazaphospholidin-2-yl]thymidine (434937-14-1) → C51H70N5O11PSi2 (434937-18-5,434937-19-6)

Guidance literature:

With 1-(cyanomethyl)pyrrolidinium trifluoromethanesulfonate; In acetonitrile;

DOI:10.1016/j.bmcl.2006.03.076

upstream raw materials:

5'-O-tert-butyldiphenylsilylthymidine

(5S)-2-chloro-3-methyl-5-phenyl-1,3,2-oxazaphospholidine

N-methyl (S)-2-hydroxy-2-phenylethylamine

Downstream raw materials:

C₅₁H₇₀N₅O₁₁PSi₂

C₄₂H₅₉N₄O₁₁PSSi₂