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

Base Information

• Chemical Name: 5-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-2-fluoro-3-[hydroxy(methyl)amino]-D-arabino-1,4-lactone
• CAS No.: 688036-02-4
• Molecular Formula: C₂₂H₂₈FNO₄Si
• Molecular Weight: 417.553
• Mol file: 688036-02-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 5-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-2-fluoro-3-[hydroxy(methyl)amino]-D-arabino-1,4-lactone 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: 65.0%

N-methylhydroxyamine hydrochloride (4229-44-1) + 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-5H-furan-2-one → 5-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-2-fluoro-3-[hydroxy(methyl)amino]-D-arabino-1,4-lactone (688036-02-4)

Guidance literature:

N-methylhydroxyamine hydrochloride; With sodium ethanolate; In ethanol; at 20 ℃; for 0.166667h;

5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-5H-furan-2-one; In ethanol; for 5h; Heating;

DOI:10.1002/hlca.200490030

Reference yield: 89.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 5-O-[(tert-butyl)diphenylsilyl]-2,3-dideoxy-2-fluoro-3-[hydroxy(methyl)amino]-D-arabino-1,4-lactone (688036-02-4) → 5-O-[(tert-butyl)diphenylsilyl]-3-({[(tert-butyl)dimethylsilyl]oxy}(methyl)amino)-2,3-dideoxy-2-fluoro-D-arabino-1,4-lactone (367491-79-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

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-{3'-[(cyclohexylmethyl)(hydroxy)amino]-2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl}uracyl

Guidance literature:

Multi-step reaction with 8 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: 88 percent / NaBH₃CN / methanol / 0.17 h / 20 °C

8.1: 85 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

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

DOI:10.1002/hlca.200490030

upstream raw materials:

N-methylhydroxyamine hydrochloride

Downstream raw materials:

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

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

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

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