3'-Deoxy-2',3'-didehydro-5'-O-(4-methoxyphenyl)-3'-phenoxycarbonylthiomethylthymidine

Base Information

• Chemical Name: 3'-Deoxy-2',3'-didehydro-5'-O-(4-methoxyphenyl)-3'-phenoxycarbonylthiomethylthymidine
• CAS No.: 137704-10-0
• Molecular Formula: C₂₅H₂₄N₂O₇S
• Molecular Weight: 496.541
• Mol file: 137704-10-0.mol

Synonyms:3'-Deoxy-2',3'-didehydro-5'-O-(4-methoxyphenyl)-3'-phenoxycarbonylthiomethylthymidine

Chemical Property of 3'-Deoxy-2',3'-didehydro-5'-O-(4-methoxyphenyl)-3'-phenoxycarbonylthiomethylthymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-Deoxy-2',3'-didehydro-5'-O-(4-methoxyphenyl)-3'-phenoxycarbonylthiomethylthymidine

There total 9 articles about 3'-Deoxy-2',3'-didehydro-5'-O-(4-methoxyphenyl)-3'-phenoxycarbonylthiomethylthymidine 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: 49.0%

3'-Deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-β-D-thymidine (137704-09-7) + phenylcarbonochloridothioate (1005-56-7) → 3'-Deoxy-2',3'-didehydro-5'-O-(4-methoxyphenyl)-3'-phenoxycarbonylthiomethylthymidine (137704-10-0)

Guidance literature:

With pyridine; dmap; for 2h; Ambient temperature;

DOI:10.1055/s-1990-26969

Reference yield:

3-Deoxy-5-O-(4-methoxyphenyl)-3-methylidene-D-erythro-pentofuranose → 3'-Deoxy-2',3'-didehydro-5'-O-(4-methoxyphenyl)-3'-phenoxycarbonylthiomethylthymidine (137704-10-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 12 h / Ambient temperature

2: 47 percent / Me₃SiCl, hexamethyldisilazane, trimethylsilyl trifluoromethylsulfonate / 1,2-dichloro-ethane / 2 h / 60 °C

3: 99 percent / KCN / methanol / 12 h / Ambient temperature

4: 49 percent / 4-dimethylaminopyridine, pyridine / 2 h / Ambient temperature

With pyridine; dmap; potassium cyanide; chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; 1,2-dichloro-ethane;

DOI:10.1055/s-1990-26969

Reference yield:

1,2-O-Isopropylidene-5-O-(4-methoxyphenyl)-α-D-xylofuranose (137704-03-1) → 3'-Deoxy-2',3'-didehydro-5'-O-(4-methoxyphenyl)-3'-phenoxycarbonylthiomethylthymidine (137704-10-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / molecular sieves (4 Angstroem), pyridinium dichromate, acetic acid / CH₂Cl₂ / 1 h / Ambient temperature

2: 1) 1.4 M s-BuLi / 1) THF, cyclohexane, -60 deg C, 2) -30 deg C, 1 h

3: Amberlite resin IRN 77 (H⁺), aq. AcOH / 12 h / Ambient temperature

4: pyridine / 12 h / Ambient temperature

5: 47 percent / Me₃SiCl, hexamethyldisilazane, trimethylsilyl trifluoromethylsulfonate / 1,2-dichloro-ethane / 2 h / 60 °C

6: 99 percent / KCN / methanol / 12 h / Ambient temperature

7: 49 percent / 4-dimethylaminopyridine, pyridine / 2 h / Ambient temperature

With pyridine; dmap; potassium cyanide; dipyridinium dichromate; chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Amberlite resin IRN 77 (H⁺); sec.-butyllithium; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1055/s-1990-26969

upstream raw materials:

3'-Deoxy-5'-O-(4-methoxyphenyl)-3'-methylidene-β-D-thymidine

phenylcarbonochloridothioate

1,2-O-Isopropylidene-5-O-(4-methoxyphenyl)-α-D-xylofuranose

3-Deoxy-1,2-O-isopropylidene-5-O-(4-methoxyphenyl)-3-methylidene-α-D-erythro-pentofuranose

Downstream raw materials:

3'-Deoxy-2',3'-didehydro-5'-O-(4-methoxyphenyl)-3'-methylthymidine

3'-Deoxy-2',3'-didehydro-3'-methylthymidine