5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2-hydroxyethyl)-2-O-para-methoxyphenyl-2'-O-phenoxythiocarbonyl-(β-D-ribofuranosyl)thymine

Base Information

Chemical Name:5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2-hydroxyethyl)-2-O-para-methoxyphenyl-2'-O-phenoxythiocarbonyl-(β-D-ribofuranosyl)thymine
CAS No.:144944-88-7
Molecular Formula:C₃₂H₄₂N₂O₈SSi
Molecular Weight:642.846
Hs Code.:

Synonyms:5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2-hydroxyethyl)-2-O-para-methoxyphenyl-2'-O-phenoxythiocarbonyl-(β-D-ribofuranosyl)thymine

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Chemical Property of 5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2-hydroxyethyl)-2-O-para-methoxyphenyl-2'-O-phenoxythiocarbonyl-(β-D-ribofuranosyl)thymine

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Technology Process of 5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2-hydroxyethyl)-2-O-para-methoxyphenyl-2'-O-phenoxythiocarbonyl-(β-D-ribofuranosyl)thymine

There total 8 articles about 5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2-hydroxyethyl)-2-O-para-methoxyphenyl-2'-O-phenoxythiocarbonyl-(β-D-ribofuranosyl)thymine 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: 87.0%

: 144944-87-6
5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2-hydroxyethyl)-2-O-para-methoxyphenyl-(β-D-ribofuranosyl)thymine

: 1005-56-7
phenylcarbonochloridothioate

: 144944-88-7
5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2-hydroxyethyl)-2-O-para-methoxyphenyl-2'-O-phenoxythiocarbonyl-(β-D-ribofuranosyl)thymine

Guidance literature:: With pyridine; In dichloromethane; 1.) 0 deg C, 1 h, 2.) refrigerator, 20 h;

Reference yield:

: 58399-76-1
3-Deoxy-3-C-(2'-hydroxyethyl)-1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-ribofuranose

: 144944-88-7
5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2-hydroxyethyl)-2-O-para-methoxyphenyl-2'-O-phenoxythiocarbonyl-(β-D-ribofuranosyl)thymine

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 0.33 h / Heating

2: 69 percent / 2.) camphorsulfonic acid / acetic acid / 70 °C / 1.) 15 min, 2.) 12 min

3: 91 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 6 h / Heating

4: 100 percent / methanolic ammonia / 10 h / Ambient temperature

5: 86 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

6: 87 percent / pyridine / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) refrigerator, 20 h

With pyridine; 1H-imidazole; camphor-10-sulfonic acid; ammonia; triphenylphosphine; diethylazodicarboxylate; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

Reference yield:

: 150-76-5
4-methoxy-phenol

: 144944-88-7
5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-C-(2-hydroxyethyl)-2-O-para-methoxyphenyl-2'-O-phenoxythiocarbonyl-(β-D-ribofuranosyl)thymine

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 0.33 h / Heating

2: 69 percent / 2.) camphorsulfonic acid / acetic acid / 70 °C / 1.) 15 min, 2.) 12 min

3: 91 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 6 h / Heating

4: 100 percent / methanolic ammonia / 10 h / Ambient temperature

5: 86 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

6: 87 percent / pyridine / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) refrigerator, 20 h

With pyridine; 1H-imidazole; camphor-10-sulfonic acid; ammonia; triphenylphosphine; diethylazodicarboxylate; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;