5'-amino-5'-deoxyuridine

Base Information

• Chemical Name: 5'-amino-5'-deoxyuridine
• CAS No.: 24514-44-1
• Molecular Formula: C₉H₁₃N₃O₅
• Molecular Weight: 243.219
• Mol file: 24514-44-1.mol

Synonyms:

Chemical Property of 5'-amino-5'-deoxyuridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-amino-5'-deoxyuridine

There total 12 articles about 5'-amino-5'-deoxyuridine 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: 96.0%

5'-azido-5'-deoxyuridine (39483-48-2) → 5'-amino-5'-deoxyuridine (24514-44-1,34718-92-8,71295-94-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 3h;

DOI:10.1021/ja206304k

Reference yield:

uridine (58-96-8) → 5'-amino-5'-deoxyuridine (24514-44-1,34718-92-8,71295-94-8)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 1.5 h / 40 °C / Inert atmosphere; Molecular sieve

2: pyridine / dichloromethane / 2.5 h / Inert atmosphere; Reflux

3: sodium azide / N,N-dimethyl-formamide / 18 h / 45 °C / Inert atmosphere

4: water; trifluoroacetic acid / 0.67 h / In air

5: palladium 10% on activated carbon; hydrogen / methanol / 1.25 h / In air

With pyridine; sodium azide; palladium 10% on activated carbon; water; hydrogen; toluene-4-sulfonic acid; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja2011109

Reference yield:

2',3'-O-isopropylideneuridine (362-43-6) → 5'-amino-5'-deoxyuridine (24514-44-1,34718-92-8,71295-94-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / dichloromethane / 2.5 h / Inert atmosphere; Reflux

2: sodium azide / N,N-dimethyl-formamide / 18 h / 45 °C / Inert atmosphere

3: water; trifluoroacetic acid / 0.67 h / In air

4: palladium 10% on activated carbon; hydrogen / methanol / 1.25 h / In air

With pyridine; sodium azide; palladium 10% on activated carbon; water; hydrogen; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja2011109

upstream raw materials:

uridylyl (3'-5') 5'-amino-5'-deoxyuridine

5'-azido-5'-deoxyuridine

2',3'-O-isopropylideneuridine

2',3'-O-isopropylidene-5'-O-tosyluridine

Downstream raw materials:

C₂₂H₁₉F₂N₃O₇

C₂₄H₃₃N₃O₇

C₂₂H₂₃Cl₂N₃O₈

C₁₈H₁₉N₃O₆

Refernces

• 1、 Hiratsuka, Tomoshige,Suzuki, Hideaki,Kariya, Ryo,Seo, Takashi,Minami, Atsushi,Oikawa, Hideaki. "Biosynthesis of the structurally unique polycyclopropanated polyketide-nucleoside hybrid jawsamycin (FR-900848)". . p. 5423 - 5426. Retrieved 2014.
• 2、 Cui, Zheng,Liu, Xiaodong,Overbay, Jonathan,Cai, Wenlong,Wang, Xiachang,Lemke, Anke,Wiegmann, Daniel,Niro, Giuliana,Thorson, Jon S.,Ducho, Christian,Van Lanen, Steven G.. "Enzymatic Synthesis of the Ribosylated Glycyl-Uridine Disaccharide Core of Peptidyl Nucleoside Antibiotics". . p. 7239 - 7249. Retrieved 2018/05/29.