[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)

Base Information

Chemical Name:[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)
CAS No.:859210-62-1
Molecular Formula:C₃₀H₄₄N₄O₉SSi
Molecular Weight:664.852
Hs Code.:

[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)

Synonyms:[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)

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Chemical Property of [1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)

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Technology Process of [1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)

There total 6 articles about [1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole) 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: 67.0%

: 859210-59-6
1-(3'-amino-5'-O-benzyl-2'-O-tert-butyldimethylsilyl-3'-C-cyano-3'-deoxy-3'-N-mesyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine

: 859210-62-1
[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)

Guidance literature:: With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/jm050091g

Reference yield:

: 3-amino-5-O-benzyl-3-C-cyano-3-deoxy-3-N-mesyl-1,2-O-sulfinyl-α-D-ribofuranose

: 859210-62-1
[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)

Guidance literature:: Multi-step reaction with 4 steps

1.1: ammonium sulfate; hexamethyldisilazane / Heating

1.2: 2 h / 125 °C

1.3: 82 percent / TBAF*3H₂O / tetrahydrofuran / 0.5 h

2.1: 89 percent / imidazole / dimethylformamide / 20 °C

3.1: 88 percent / pyridine / CH₂Cl₂ / 8.5 h / 20 °C

4.1: 67 percent / n-BuLi; diisopropylamine / tetrahydrofuran / 1 h / -78 °C

With pyridine; 1H-imidazole; ammonium sulfate; n-butyllithium; diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm050091g

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 859210-62-1
[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(2''-H-4''-amino-2'',3''-dihydro-1'',1''-dioxo-isothiazole)

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / imidazole / dimethylformamide / 20 °C

2: 88 percent / pyridine / CH₂Cl₂ / 8.5 h / 20 °C

3: 67 percent / n-BuLi; diisopropylamine / tetrahydrofuran / 1 h / -78 °C

With pyridine; 1H-imidazole; n-butyllithium; diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm050091g