1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)thymidine

Base Information

Chemical Name:1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)thymidine
CAS No.:612485-26-4
Molecular Formula:C₁₈H₁₅N₃O₅
Molecular Weight:353.334
Hs Code.:

Synonyms:1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)thymidine

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Chemical Property of 1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)thymidine

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Technology Process of 1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)thymidine

There total 6 articles about 1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)thymidine 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: 96.0%

: 612485-20-8
1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)thymine

: 612485-26-4
1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)thymidine

Guidance literature:: With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(03)01074-3

Reference yield:

: 98-88-4
benzoyl chloride

: 612485-26-4
1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)thymidine

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

2: CF₃CO₂H / H₂O / 6 h

3: 32 g / pyridine / 12 h / 20 °C

4: 86 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 10 h / Heating

5: 96 percent / 4-(dimethylamino)pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4020(03)01074-3

Reference yield:

: 3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-L-ribofuranose

: 612485-26-4
1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)thymidine

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

2: CF₃CO₂H / H₂O / 6 h

3: 32 g / pyridine / 12 h / 20 °C

4: 86 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 10 h / Heating

5: 96 percent / 4-(dimethylamino)pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4020(03)01074-3