3',5'-di-O-p-toluoyl-α-2'-deoxythymidine

Base Information

• Chemical Name: 3',5'-di-O-p-toluoyl-α-2'-deoxythymidine
• CAS No.: 4784-41-2
• Molecular Formula: C₂₆H₂₆N₂O₇
• Molecular Weight: 478.502
• Mol file: 4784-41-2.mol

Synonyms:

Chemical Property of 3',5'-di-O-p-toluoyl-α-2'-deoxythymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3',5'-di-O-p-toluoyl-α-2'-deoxythymidine

There total 9 articles about 3',5'-di-O-p-toluoyl-α-2'-deoxythymidine 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: 37.0%

3',5'-di-O-toluoylthymidine (4449-39-2) → 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)thymine (4784-41-2)

Guidance literature:

With sulfuric acid; acetic anhydride; In dichloromethane; acetonitrile; for 1h; Ambient temperature;

DOI:10.1002/jhet.5570320542

Reference yield:

4-methyl-benzoyl chloride (874-60-2) → 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)thymine (4784-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / pyridine / 1 h / 20 °C

2: 81 percent Spectr_. / hexamethyldisilazane; trimethylsilyl triflate / acetonitrile / 20 h / 30 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile;

DOI:10.1002/1099-0690(20021)2002:1<87::AID-EJOC87>3.0.CO;2-B

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)thymine (4784-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / pyridine / 1 h / 20 °C

2: 81 percent Spectr_. / hexamethyldisilazane; trimethylsilyl triflate / acetonitrile / 20 h / 30 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile;

DOI:10.1002/1099-0690(20021)2002:1<87::AID-EJOC87>3.0.CO;2-B

upstream raw materials:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose

N,O-Bis(trimethylsilyl)acetamide

Downstream raw materials:

3',5'-di-O-p-toluoyl-α-2'-deoxythymidine

α-deoxythymidine

Phosphoramidous acid (2R,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester

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

Refernces

• 1、 Sato, Yuichi,Tateno, Gohsuke,Seio, Kohji,Sekine, Mitsuo. "Substituent and solvent effects of TMS triflate mediated C1′ epimerization of β-thymidine to α-thymidine". . p. 87 - 93. Retrieved 2007/10/03.
• 2、 Shinozuka, Kazuo,Hirota, Yoshiki,Morita, Tsutomu,Sawai, Hiroaki. "FACILE STEREOSPECIFIC SYNTHESIS OF α-ANOMERIC 2'-DEOXYNUCLEOSIDES". . p. 2117 - 2121. Retrieved 2007/10/02.