5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine

Base Information

• Chemical Name: 5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine
• CAS No.: 175013-49-7
• Molecular Formula: C₂₆H₂₉N₃O₇Si
• Molecular Weight: 523.618
• Mol file: 175013-49-7.mol

Synonyms:5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine

Chemical Property of 5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine

There total 6 articles about 5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine 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: 79.0%

2'-(benzyloxyamino)-5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxyuridine (175013-53-3) → 5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine (175013-49-7)

Guidance literature:

palladium on activated charcoal; In ethanol; Ambient temperature;

DOI:10.1016/S0960-894X(98)00336-9

Reference yield: 9.0%

3'-O-(t-butyldimethylsilyloxyamino)carbonyl-5'-O-tert-butyldiphenylsilyl-2,2'-anhydrouridine (175013-47-5) → 1-[(3aR,4R,6R,6aS)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-hexahydro-furo[3,4-d]oxazol-4-yl]-1H-pyrimidine-2,4-dione + 5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine (175013-49-7) + C32H43N3O7Si2

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 23 ℃;

DOI:10.1016/0040-4020(96)00870-8

Reference yield:

2,2'-Anhydrouridine (3736-77-4) → 5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine (175013-49-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / pyridine / dimethylformamide

2: pyridine

3: pyridine

4: 36 percent / DBU / tetrahydrofuran / 23 °C

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(96)00870-8

upstream raw materials:

3'-O-(t-butyldimethylsilyloxyamino)carbonyl-5'-O-tert-butyldiphenylsilyl-2,2'-anhydrouridine

2'-(benzyloxyamino)-5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxyuridine

2,2'-Anhydrouridine

tert-butylchlorodiphenylsilane

Downstream raw materials:

5'-O-(tert-butyldiphenylsilyl)-2'-amino>-2'-deoxyuridine

5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine

5'-O-(tert-butyldiphenylsilyl)-2'-deoxy-2-(N-hydroxy-N-methylamino)uridine

3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-2'-deoxy-2'-<(2-tetrahydrofuranyl)oxyamino>uridine