N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl phosphate)

Base Information

Chemical Name:N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl phosphate)
CAS No.:529495-84-9
Molecular Formula:C₃₉H₆₁N₄O₇PS₃
Molecular Weight:825.108
Hs Code.:

Synonyms:N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl phosphate)

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Chemical Property of N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl phosphate)

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Technology Process of N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl phosphate)

There total 7 articles about N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl 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: 23.0%

: 141186-19-8
Diisopropyl-phosphoramidous acid 2-cyano-ethyl ester hexadecyl ester

: 529495-83-8
N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine

: 529495-84-9
N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl phosphate)

Guidance literature:: Diisopropyl-phosphoramidous acid 2-cyano-ethyl ester hexadecyl ester; N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine; With 1H-tetrazole; In tetrahydrofuran; acetonitrile; at 20 ℃;

With ethylmethyldioxirane; In tetrahydrofuran; dichloromethane; acetonitrile; for 2h;
DOI:10.1016/S0968-0896(02)00460-1

Reference yield:

: 110171-24-9
(R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)furan-2(5H)-one

: 529495-84-9
N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl phosphate)

Guidance literature:: Multi-step reaction with 7 steps

1.1: 81 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: DIBAL / toluene; hexane / 1 h / -70 °C

3.1: 65 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

4.1: HMDS; (NH₄)2SO₄ / Heating

4.2: 51 percent / TMSOTf / acetonitrile / 0.75 h / 0 - 20 °C

5.1: 73 percent / HOBt / dimethylformamide / 20 °C

6.1: 75 percent / TBAF / tetrahydrofuran / 2 h

7.1: tetrazole / tetrahydrofuran; acetonitrile / 20 °C

7.2: 23 percent / ethyl(methyl)dioxirane / tetrahydrofuran; acetonitrile; CH₂Cl₂ / 2 h

With pyridine; 1H-tetrazole; ammonium sulfate; n-butyllithium; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; benzotriazol-1-ol; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0968-0896(02)00460-1

Reference yield:

: (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-ol

: 529495-84-9
N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl phosphate)

Guidance literature:: Multi-step reaction with 5 steps

1.1: 65 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

2.1: HMDS; (NH₄)2SO₄ / Heating

2.2: 51 percent / TMSOTf / acetonitrile / 0.75 h / 0 - 20 °C

3.1: 73 percent / HOBt / dimethylformamide / 20 °C

4.1: 75 percent / TBAF / tetrahydrofuran / 2 h

5.1: tetrazole / tetrahydrofuran; acetonitrile / 20 °C

5.2: 23 percent / ethyl(methyl)dioxirane / tetrahydrofuran; acetonitrile; CH₂Cl₂ / 2 h

With pyridine; 1H-tetrazole; ammonium sulfate; tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0968-0896(02)00460-1