1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}thymine

Base Information

Chemical Name:1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}thymine
CAS No.:537690-82-7
Molecular Formula:C₃₇H₃₄N₂O₈
Molecular Weight:634.686
Hs Code.:

Synonyms:1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}thymine

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Chemical Property of 1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}thymine

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Technology Process of 1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}thymine

There total 10 articles about 1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}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: 81.8%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 325684-00-2
1-(2′-O-benzoyl-α-L-threofuranosyl)thymine

: 537690-82-7
1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}thymine

Guidance literature:: With 2,4,6-trimethyl-pyridine; In dichloromethane; at 20 ℃;
DOI:10.1002/hlca.200290000

Reference yield:

: 1446785-28-9
2-O-Benzoyl-3-O-tert-butyldiphenylsilyl-L-threonolactone

: 537690-82-7
1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}thymine

Guidance literature:: Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / 1,2-dimethoxyethane; toluene / 0.5 h / -78 °C / Inert atmosphere

2.1: dmap / dichloromethane / 1.67 h / -78 - 20 °C / Inert atmosphere

3.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 60 °C / Inert atmosphere

3.2: 2 h / 60 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere

5.1: pyridine; dmap / 16 h / 80 °C / Inert atmosphere

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; toluene; acetonitrile; 3.1: |Vorbrueggen Nucleoside Synthesis / 3.2: |Vorbrueggen Nucleoside Synthesis;
DOI:10.1021/acs.joc.5b02768

Reference yield:

: 91345-19-6
2′-O-benzoyl-L-threonolactone

: 537690-82-7
1-{2'-O-benzoyl-3'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-L-threofuranosyl}thymine

Guidance literature:: Multi-step reaction with 6 steps

1.1: dmap; 1H-imidazole / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / 1,2-dimethoxyethane; toluene / 0.5 h / -78 °C / Inert atmosphere

3.1: dmap / dichloromethane / 1.67 h / -78 - 20 °C / Inert atmosphere

4.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 60 °C / Inert atmosphere

4.2: 2 h / 60 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere

6.1: pyridine; dmap / 16 h / 80 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; toluene; acetonitrile; 4.1: |Vorbrueggen Nucleoside Synthesis / 4.2: |Vorbrueggen Nucleoside Synthesis;
DOI:10.1021/acs.joc.5b02768