2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine

Base Information

• Chemical Name: 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine
• CAS No.: 158532-72-0
• Molecular Formula: C₁₀H₁₂N₂O₅
• Molecular Weight: 240.216
• Mol file: 158532-72-0.mol

Synonyms:2',3'-Didehydro-2',3'-dideoxy-5-(hydroxymethyl)uridine

Chemical Property of 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 8.94±0.10(Predicted)
• Flash Point: °C
• PSA: 104.81000
• Density: 1.485g/cm³
• LogP: -1.11290

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine

There total 15 articles about 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine 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: 100.0%

5-t-butyldiphenylsilyloxymethyl-5'-O-t-butyldiphenylsilyl-2',3'-didehydro-2',3'-dideoxyuridine (917482-60-1) → 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine (158532-72-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h;

DOI:10.1016/j.tetlet.2006.09.083

Reference yield: 81.0%

5'-O-acetyl-2',3'-didehydro-2',3'-dideoxy-5-acetoxymethyl-uridine (210469-38-8) → 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine (158532-72-0)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 24h;

DOI:10.1080/15257770008033040

Reference yield:

2',3'-isopropylidene-5-methyl-5'-O-t-butyldiphenylsilyluridine (917482-61-2) → 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine (158532-72-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N-bromosuccinimide; benzoyl peroxide / CCl₄ / Heating

2.1: 491 mg / NaHCO₃ / H₂O; tetrahydrofuran / 20 °C

3.1: 24 percent / imidazole; DMAP / dimethylformamide / 20 °C

4.1: AcOH / H₂O / Heating

5.1: NaOH / dimethylsulfoxide; H₂O / 0.33 h / 20 °C

5.2: 41 percent / dimethylsulfoxide; H₂O / 1.5 h

6.1: 77 percent / AIBN; Bu₃SnH / toluene / 3 h / Heating

7.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h

With 1H-imidazole; dmap; sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydrogencarbonate; acetic acid; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2006.09.083

upstream raw materials:

5'-O-acetyl-2',3'-didehydro-2',3'-dideoxy-5-acetoxymethyl-uridine

5-t-butyldiphenylsilyloxymethyl-5'-O-t-butyldiphenylsilyl-2',3'-didehydro-2',3'-dideoxyuridine

2',3'-isopropylidene-5-methyl-5'-O-t-butyldiphenylsilyluridine

5-t-butyldiphenylsilyloxymethyl-5'-O-t-butyldiphenylsilyluridine

Refernces

• 1、 Chung, Raymond,Anderson, Karen S.. "Alternative synthetic routes to 2′,3′-didehydro-2′,3′-dideoxy-5-hydroxymethyluridine". . p. 8361 - 8363. Retrieved 2007/10/03.