1-(5-O-tert-butyldimethylsilyl-2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

Base Information

Chemical Name:1-(5-O-tert-butyldimethylsilyl-2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine
CAS No.:219662-01-8
Molecular Formula:C₂₂H₃₁N₃O₄SSi
Molecular Weight:461.657
Hs Code.:

Synonyms:1-(5-O-tert-butyldimethylsilyl-2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

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Chemical Property of 1-(5-O-tert-butyldimethylsilyl-2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

Chemical Property:

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Technology Process of 1-(5-O-tert-butyldimethylsilyl-2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

There total 12 articles about 1-(5-O-tert-butyldimethylsilyl-2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine 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: 90.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 219661-98-0
1-(2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

: 219662-01-8
1-(5-O-tert-butyldimethylsilyl-2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 18h;
DOI:10.1080/07328319808004318

Reference yield:

: 102339-30-0
(3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-ol

: 219662-01-8
1-(5-O-tert-butyldimethylsilyl-2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

Guidance literature:: Multi-step reaction with 9 steps

1: 88 percent / 1,2-dichloro-ethane / 3 h / Heating

2: 80 percent / (Me₃Si)3SiH, AIBN / toluene / 2 h / Heating

3: 66 percent / BF₃, Et₂O

4: pyridine

5: 89 percent / BaCO₃, NBu₄I

6: 75 percent / acetic acid / 1 h / Ambient temperature

7: 45 percent / TMSOTf, BSA / acetonitrile / 6 h / Heating

8: BCl₃ / CH₂Cl₂ / 6 h / -78 °C

9: 90 percent / imidazole / dimethylformamide / 18 h

With 1H-imidazole; benzenesulfonamide; diethyl ether; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tris-(trimethylsilyl)silane; boron trifluoride; boron trichloride; tetra-(n-butyl)ammonium iodide; barium carbonate; In pyridine; dichloromethane; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1080/07328319808004318

Reference yield:

: 41341-99-5
3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

: 219662-01-8
1-(5-O-tert-butyldimethylsilyl-2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

Guidance literature:: Multi-step reaction with 11 steps

1: aq. CF₃COOH / 3 h / 0 °C

2: 90 percent / conc. H₂SO₄ / 24 h / 0 °C

3: 88 percent / 1,2-dichloro-ethane / 3 h / Heating

4: 80 percent / (Me₃Si)3SiH, AIBN / toluene / 2 h / Heating

5: 66 percent / BF₃, Et₂O

6: pyridine

7: 89 percent / BaCO₃, NBu₄I

8: 75 percent / acetic acid / 1 h / Ambient temperature

9: 45 percent / TMSOTf, BSA / acetonitrile / 6 h / Heating

10: BCl₃ / CH₂Cl₂ / 6 h / -78 °C

11: 90 percent / imidazole / dimethylformamide / 18 h

With 1H-imidazole; benzenesulfonamide; diethyl ether; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tris-(trimethylsilyl)silane; sulfuric acid; boron trifluoride; boron trichloride; tetra-(n-butyl)ammonium iodide; barium carbonate; trifluoroacetic acid; In pyridine; dichloromethane; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1080/07328319808004318