2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde

Base Information

• Chemical Name: 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde
• CAS No.: 137233-53-5
• Molecular Formula: C₂₉H₄₆N₂O₇Si₂
• Molecular Weight: 590.864
• Mol file: 137233-53-5.mol

Synonyms:2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde

Chemical Property of 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde

There total 9 articles about 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde 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: 98.0%

2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine (137233-57-9) → 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde (137233-53-5)

Guidance literature:

DOI:10.1055/s-0029-1217742

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde (137233-53-5)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 13.5 h / 23 °C

2: NaH / dimethylformamide / 4.5 h / 0 °C

3: benzenesulfonic acid / CHCl₃ / 0.08 h / 0 °C

4: 1.) (COCl)2, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 30 min

With 1H-imidazole; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; benzenesulfonic acid; In chloroform; N,N-dimethyl-formamide;

DOI:10.1021/ja00090a018

Reference yield:

2',3'-O-bis(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)uridine (82444-76-6) → 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde (137233-53-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / dimethylformamide / 4.5 h / 0 °C

2: benzenesulfonic acid / CHCl₃ / 0.08 h / 0 °C

3: 1.) (COCl)2, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 30 min

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; benzenesulfonic acid; In chloroform; N,N-dimethyl-formamide;

DOI:10.1021/ja00090a018

upstream raw materials:

2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine

tert-butyldimethylsilyl chloride

2',3'-O-bis(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)uridine

5'-dimethoxytrityluridine

Downstream raw materials:

C₃₅H₅₉N₃O₈Si₂

C₃₅H₅₉N₃O₈Si₂

C₄₃H₆₃N₃O₁₀Si₂

C₄₃H₆₃N₃O₁₀Si₂