1-(5'-(4-toluenesulfonyl)-3'-deoxy-2'-tert-butyldimethylsilyloxy-α-L-arabinofuranosyl)uracil

Base Information

Chemical Name:1-(5'-(4-toluenesulfonyl)-3'-deoxy-2'-tert-butyldimethylsilyloxy-α-L-arabinofuranosyl)uracil
CAS No.:286939-19-3
Molecular Formula:C₂₂H₃₂N₂O₇SSi
Molecular Weight:496.657
Hs Code.:

Synonyms:1-(5'-(4-toluenesulfonyl)-3'-deoxy-2'-tert-butyldimethylsilyloxy-α-L-arabinofuranosyl)uracil

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Chemical Property of 1-(5'-(4-toluenesulfonyl)-3'-deoxy-2'-tert-butyldimethylsilyloxy-α-L-arabinofuranosyl)uracil

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Technology Process of 1-(5'-(4-toluenesulfonyl)-3'-deoxy-2'-tert-butyldimethylsilyloxy-α-L-arabinofuranosyl)uracil

There total 6 articles about 1-(5'-(4-toluenesulfonyl)-3'-deoxy-2'-tert-butyldimethylsilyloxy-α-L-arabinofuranosyl)uracil 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%

: 98-59-9
p-toluenesulfonyl chloride

: 286939-18-2
1-(3-deoxy-2-tert-butyldimethylsiloxy-α-L-arabinofuranosyl)uracil

: 286939-19-3
1-(5'-(4-toluenesulfonyl)-3'-deoxy-2'-tert-butyldimethylsilyloxy-α-L-arabinofuranosyl)uracil

Guidance literature:: With pyridine; at 20 ℃; for 25h;
DOI:10.1021/ja003292c

Reference yield:

: 92985-14-3
N¹-(tert-Butyl 2,3-O-isopropylidene-β-D-ribofuranosyluronate)uracil

: 286939-19-3
1-(5'-(4-toluenesulfonyl)-3'-deoxy-2'-tert-butyldimethylsilyloxy-α-L-arabinofuranosyl)uracil

Guidance literature:: Multi-step reaction with 6 steps

1.1: t-BuOK / 2-methyl-propan-2-ol

1.2: AcOH / 2-methyl-propan-2-ol / pH 7.5 - 8

2.1: 2.39 g / imidazole / dimethylformamide / 1 h / 20 °C

3.1: 85 percent / H₂ / Pd/C / methanol / 0.67 h / 760 Torr

4.1: TFA / CH₂Cl₂ / 0.17 h / 20 °C

5.1: EtOCOCl; Et₃N / tetrahydrofuran / 2 h / 20 °C

5.2: 44.8 mg / aq. NaBH₄ / tetrahydrofuran / 1 h / 0 °C

6.1: 90 percent / pyridine / 25 h / 20 °C

With pyridine; 1H-imidazole; potassium tert-butylate; hydrogen; chloroformic acid ethyl ester; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja003292c

Reference yield:

: tert-butyl (4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-4,5-dihydrofuran-2-carboxylate

: 286939-19-3
1-(5'-(4-toluenesulfonyl)-3'-deoxy-2'-tert-butyldimethylsilyloxy-α-L-arabinofuranosyl)uracil

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2.39 g / imidazole / dimethylformamide / 1 h / 20 °C

2.1: 85 percent / H₂ / Pd/C / methanol / 0.67 h / 760 Torr

3.1: TFA / CH₂Cl₂ / 0.17 h / 20 °C

4.1: EtOCOCl; Et₃N / tetrahydrofuran / 2 h / 20 °C

4.2: 44.8 mg / aq. NaBH₄ / tetrahydrofuran / 1 h / 0 °C

5.1: 90 percent / pyridine / 25 h / 20 °C

With pyridine; 1H-imidazole; hydrogen; chloroformic acid ethyl ester; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja003292c