3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate

Base Information

Chemical Name:3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate
CAS No.:249286-87-1
Molecular Formula:C₃₂H₃₆F₃N₄O₁₂P
Molecular Weight:756.626
Hs Code.:

Synonyms:3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate

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Chemical Property of 3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate

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Technology Process of 3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate

There total 6 articles about 3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate 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%

: 96-35-5
glycolic acid methyl ester

: 249286-85-9
3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-<(2-cyanoethyl)-N,N-diisopropyl> phosphoramidite

: 249286-87-1
3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate

Guidance literature:: With 1H-tetrazole; tert.-butylhydroperoxide; In acetonitrile; for 1.5h;
DOI:10.1016/S0008-6215(99)00074-9

Reference yield:

: 98-88-4
benzoyl chloride

: 249286-87-1
3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / pyridine / 20 °C

2: 94 percent / TBAF*3H₂O / tetrahydrofuran / 5 h

3: 85 percent / tris(triphenylphosphine)-palladium(II) chloride; anhyd copper(I) iodide / triethylamine / 2 h / 50 °C

4: 86 percent / N,N-diisopropylethylamine / acetonitrile / 0.5 h

5: 83 percent / 1-H tetrazole; tert-butylyhydroperoxide / acetonitrile / 1.5 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; copper(l) iodide; tris(triphenylphosphine)-palladium(II) dichloride; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; triethylamine; acetonitrile; 1: Acylation / 2: desilylation / 3: Heck reaction / 4: Substitution / 5: Substitution;
DOI:10.1016/S0008-6215(99)00074-9

Reference yield:

: 134218-81-8
5’-O-(tert-butyldimethylsilyl)-2’-deoxy-5-iodouridine

: 249286-87-1
3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / pyridine / 20 °C

2: 94 percent / TBAF*3H₂O / tetrahydrofuran / 5 h

3: 85 percent / tris(triphenylphosphine)-palladium(II) chloride; anhyd copper(I) iodide / triethylamine / 2 h / 50 °C

4: 86 percent / N,N-diisopropylethylamine / acetonitrile / 0.5 h

5: 83 percent / 1-H tetrazole; tert-butylyhydroperoxide / acetonitrile / 1.5 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; copper(l) iodide; tris(triphenylphosphine)-palladium(II) dichloride; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; triethylamine; acetonitrile; 1: Acylation / 2: desilylation / 3: Heck reaction / 4: Substitution / 5: Substitution;
DOI:10.1016/S0008-6215(99)00074-9