O-(2R,3R,5S)-2-[2'-(tert-butyldiphenylsilyloxy)ethyl]-5-[(p-fluorophenoxy)methyl]tetrahydrofuran-3-yl-1H-imidazole-1-carbothioate

Base Information

• Chemical Name: O-(2R,3R,5S)-2-[2'-(tert-butyldiphenylsilyloxy)ethyl]-5-[(p-fluorophenoxy)methyl]tetrahydrofuran-3-yl-1H-imidazole-1-carbothioate
• CAS No.: 1449521-33-8
• Molecular Formula: C₃₃H₃₇FN₂O₄SSi
• Molecular Weight: 604.818
• Mol file: 1449521-33-8.mol

Synonyms:O-(2R,3R,5S)-2-[2'-(tert-butyldiphenylsilyloxy)ethyl]-5-[(p-fluorophenoxy)methyl]tetrahydrofuran-3-yl-1H-imidazole-1-carbothioate

Chemical Property of O-(2R,3R,5S)-2-[2'-(tert-butyldiphenylsilyloxy)ethyl]-5-[(p-fluorophenoxy)methyl]tetrahydrofuran-3-yl-1H-imidazole-1-carbothioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2R,3R,5S)-2-[2'-(tert-butyldiphenylsilyloxy)ethyl]-5-[(p-fluorophenoxy)methyl]tetrahydrofuran-3-yl-1H-imidazole-1-carbothioate

There total 1 articles about O-(2R,3R,5S)-2-[2'-(tert-butyldiphenylsilyloxy)ethyl]-5-[(p-fluorophenoxy)methyl]tetrahydrofuran-3-yl-1H-imidazole-1-carbothioate 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: 83.0%

C29H35FO4Si (1263497-40-0) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → O-(2R,3R,5S)-2-[2'-(tert-butyldiphenylsilyloxy)ethyl]-5-[(p-fluorophenoxy)methyl]tetrahydrofuran-3-yl-1H-imidazole-1-carbothioate (1449521-33-8)

Guidance literature:

In tetrahydrofuran; at 70 ℃; for 24h;

DOI:10.1055/s-0033-1338934

Reference yield: 89.0%

O-(2R,3R,5S)-2-[2'-(tert-butyldiphenylsilyloxy)ethyl]-5-[(p-fluorophenoxy)methyl]tetrahydrofuran-3-yl-1H-imidazole-1-carbothioate (1449521-33-8) → (2S,5S)-2-[2′-(tert-butyldiphenylsilyloxy)ethyl]-5-[(4-fluorophenoxy)methyl]tetrahydrofuran (1449521-34-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 120 ℃; for 3h;

DOI:10.1055/s-0033-1338934

Reference yield:

O-(2R,3R,5S)-2-[2'-(tert-butyldiphenylsilyloxy)ethyl]-5-[(p-fluorophenoxy)methyl]tetrahydrofuran-3-yl-1H-imidazole-1-carbothioate (1449521-33-8) → (2S,5S)-2-[(4-fluorophenoxy)methyl]-5-vinyltetrahydrofuran (1449521-37-2)

Guidance literature:

Multi-step reaction with 4 steps

1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 3 h / 120 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h

3: triphenylphosphine; iodine; 1H-imidazole / tetrahydrofuran / 4 h / 0 °C

4: potassium tert-butylate / tetrahydrofuran / 48 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1055/s-0033-1338934

upstream raw materials:

C₂₉H₃₅FO₄Si

1,1'-Thiocarbonyldiimidazole

Downstream raw materials:

(2S,5S)-2-[2′-(tert-butyldiphenylsilyloxy)ethyl]-5-[(4-fluorophenoxy)methyl]tetrahydrofuran

(2S,5S)-5-[(4-fluorophenoxy)methyl]-2-[1′-hydroxyethyl]tetrahydrofuran

(2S,5S)-2-[(4-fluorophenoxy)methyl]-5-[2'-(iodoethyl)]tetrahydrofuran

(2S,5S)-2-[(4-fluorophenoxy)methyl]-5-vinyltetrahydrofuran