1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-[hydroxy(2-methylpropyl)amino]-β-D-arabinofuranosyl}uracil

Base Information

• Chemical Name: 1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-[hydroxy(2-methylpropyl)amino]-β-D-arabinofuranosyl}uracil
• CAS No.: 367491-85-8
• Molecular Formula: C₂₉H₃₈FN₃O₅Si
• Molecular Weight: 555.722
• Mol file: 367491-85-8.mol

Synonyms:1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-[hydroxy(2-methylpropyl)amino]-β-D-arabinofuranosyl}uracil

Chemical Property of 1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-[hydroxy(2-methylpropyl)amino]-β-D-arabinofuranosyl}uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-[hydroxy(2-methylpropyl)amino]-β-D-arabinofuranosyl}uracil

There total 8 articles about 1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-[hydroxy(2-methylpropyl)amino]-β-D-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: 92.0%

isobutyraldehyde (78-84-2) + 1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-(hydroxyamino)-β-D-arabinofuranosyl}uracil (367491-83-6) → 1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-[hydroxy(2-methylpropyl)amino]-β-D-arabinofuranosyl}uracil (367491-85-8)

Guidance literature:

isobutyraldehyde; 1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-(hydroxyamino)-β-D-arabinofuranosyl}uracil; In methanol; at 20 ℃; for 0.166667h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 0.166667h;

DOI:10.1002/hlca.200490030

Reference yield:

5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-5H-furan-2-one → 1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-[hydroxy(2-methylpropyl)amino]-β-D-arabinofuranosyl}uracil (367491-85-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: EtONa / ethanol / 0.17 h / 20 °C

1.2: 65 percent / ethanol / 5 h / Heating

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

3.1: DIBAL [(tBu)2AlH] / CH₂Cl₂; hexane / 1 h / -78 °C

4.1: MsCl; Et₃N / Bu₃N / CH₂Cl₂ / -40 °C

4.2: 1 h / 20 °C

5.1: CHCl₃ / Heating

6.1: 99 percent / HF / acetonitrile; H₂O / 1 h / 20 °C

7.1: DDQ / CH₂Cl₂ / 0.5 h / 20 °C

7.2: 57 percent / NH₂OH*HCl / methanol / 1 h / 50 °C

8.1: methanol / 0.17 h / 20 °C

8.2: 92 percent / NaBH₃CN / methanol / 0.17 h / 20 °C

With 1H-imidazole; hydrogen fluoride; sodium ethanolate; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tributyl-amine; In methanol; ethanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.200490030

Reference yield:

5-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-2-fluoro-3-[hydroxy(methyl)amino]-D-arabino-1,4-lactone (688036-02-4) → 1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-[hydroxy(2-methylpropyl)amino]-β-D-arabinofuranosyl}uracil (367491-85-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 89 percent / imidazole / dimethylformamide / 20 °C

2.1: DIBAL [(tBu)2AlH] / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: MsCl; Et₃N / Bu₃N / CH₂Cl₂ / -40 °C

3.2: 1 h / 20 °C

4.1: CHCl₃ / Heating

5.1: 99 percent / HF / acetonitrile; H₂O / 1 h / 20 °C

6.1: DDQ / CH₂Cl₂ / 0.5 h / 20 °C

6.2: 57 percent / NH₂OH*HCl / methanol / 1 h / 50 °C

7.1: methanol / 0.17 h / 20 °C

7.2: 92 percent / NaBH₃CN / methanol / 0.17 h / 20 °C

With 1H-imidazole; hydrogen fluoride; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tributyl-amine; In methanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.200490030

upstream raw materials:

isobutyraldehyde

1-{5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-2'-fluoro-3'-(hydroxyamino)-β-D-arabinofuranosyl}uracil

5-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-2-fluoro-3-[hydroxy(methyl)amino]-D-arabino-1,4-lactone

5-O-[(tert-butyl)diphenylsilyl]-3-({[(tert-butyl)dimethylsilyl]oxy}(methyl)amino)-2,3-dideoxy-2-fluoro-D-arabino-1,4-lactone