[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(4''-amino-2'',3''-dihydro-2''-N-methyl-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''-(4''-amino-2'',3''-dihydro-2''-N-methyl-1'',1''-dioxo-isothiazole)
CAS No.:859210-68-7
Molecular Formula:C₃₁H₄₆N₄O₉SSi
Molecular Weight:678.879
Hs Code.:

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

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

There total 9 articles about [1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(4''-amino-2'',3''-dihydro-2''-N-methyl-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: 51.0%

: 859210-67-6
1-(3'-amino-5'-O-benzyl-2'-O-tert-butyldimethylsilyl-3'-C-cyano-3'-deoxy-3'-N-mesyl-3'-N-methyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine

: 859210-68-7
[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(4''-amino-2'',3''-dihydro-2''-N-methyl-1'',1''-dioxo-isothiazole)

Guidance literature:: With caesium carbonate; In acetonitrile; at 60 ℃; for 1.75h; ultrasonification;
DOI:10.1021/jm050091g

Reference yield:

: 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

: 859210-68-7
[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(4''-amino-2'',3''-dihydro-2''-N-methyl-1'',1''-dioxo-isothiazole)

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / K₂CO₃ / acetone / 1.75 h / Heating

2: 51 percent / Cs₂CO₃ / acetonitrile / 1.75 h / 60 °C / ultrasonification

With potassium carbonate; caesium carbonate; In acetone; acetonitrile;
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

: 859210-68-7
[1-(5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine]-3'-spiro-3''-(4''-amino-2'',3''-dihydro-2''-N-methyl-1'',1''-dioxo-isothiazole)

Guidance literature:: Multi-step reaction with 5 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: 81 percent / K₂CO₃ / acetone / 1.75 h / Heating

5.1: 51 percent / Cs₂CO₃ / acetonitrile / 1.75 h / 60 °C / ultrasonification

With pyridine; 1H-imidazole; ammonium sulfate; potassium carbonate; caesium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jm050091g