2'-O-tert-butyldimethylsilyl-3',5'-dideoxy-3'-carboxymethyl-5'-methoxytritylaminouridine triethylammonium salt

Base Information

• Chemical Name: 2'-O-tert-butyldimethylsilyl-3',5'-dideoxy-3'-carboxymethyl-5'-methoxytritylaminouridine triethylammonium salt
• CAS No.: 817622-77-8
• Molecular Formula: C₆H₁₅N*C₃₇H₄₅N₃O₇Si
• Molecular Weight: 773.058
• Mol file: 817622-77-8.mol

Synonyms:

Chemical Property of 2'-O-tert-butyldimethylsilyl-3',5'-dideoxy-3'-carboxymethyl-5'-methoxytritylaminouridine triethylammonium salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-tert-butyldimethylsilyl-3',5'-dideoxy-3'-carboxymethyl-5'-methoxytritylaminouridine triethylammonium salt

There total 6 articles about 2'-O-tert-butyldimethylsilyl-3',5'-dideoxy-3'-carboxymethyl-5'-methoxytritylaminouridine triethylammonium salt 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:

5'-amino-2'-O-tert butyldimethylsilyl-3’-carboxymethyl-3’,5'-dideoxyuridine (1001325-72-9) + triethylamine carbonate (15715-58-9) + mono-4-methoxytrityl chloride (14470-28-1) → 2'-O-tert-butyldimethylsilyl-3',5'-dideoxy-3'-carboxymethyl-5'-methoxytritylaminouridine triethylammonium salt (817622-77-8)

Guidance literature:

5'-amino-2'-O-tert butyldimethylsilyl-3’-carboxymethyl-3’,5'-dideoxyuridine; mono-4-methoxytrityl chloride; With pyridine; at 20 ℃;

triethylamine carbonate; In water;

DOI:10.1039/c3ob42532k

Reference yield:

5'-azido-5'-deoxy-2'-O-tert butyldimethylsilyluridine → 2'-O-tert-butyldimethylsilyl-3',5'-dideoxy-3'-carboxymethyl-5'-methoxytritylaminouridine triethylammonium salt (817622-77-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Dess-Martin periodane / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 3.5 h / 20 °C

4.1: pyridine / 3 h / 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

With pyridine; palladium 10% on activated carbon; hydrogen; Dess-Martin periodane; In dichloromethane; water; tert-butyl alcohol; 2.1: |Wittig Olefination;

DOI:10.1021/acs.orglett.7b01934

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2'-O-tert-butyldimethylsilyl-3',5'-dideoxy-3'-carboxymethyl-5'-methoxytritylaminouridine triethylammonium salt (817622-77-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 20 °C

2.1: Dess-Martin periodane / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 3.5 h / 20 °C

5.1: pyridine / 3 h / 20 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

With pyridine; palladium 10% on activated carbon; hydrogen; Dess-Martin periodane; In dichloromethane; water; tert-butyl alcohol; 3.1: |Wittig Olefination;

DOI:10.1021/acs.orglett.7b01934

upstream raw materials:

5'-amino-2'-O-tert butyldimethylsilyl-3’-carboxymethyl-3’,5'-dideoxyuridine

triethylamine carbonate

mono-4-methoxytrityl chloride

tert-butyldimethylsilyl chloride