Uridine, 2',3'-didehydro-2',3'-dideoxy-, 5'-benzoate

Base Information

• Chemical Name: Uridine, 2',3'-didehydro-2',3'-dideoxy-, 5'-benzoate
• CAS No.: 6038-56-8
• Molecular Formula: C16H14N2O5
• Molecular Weight: 314.298
• Mol file: 6038-56-8.mol

Synonyms:

Chemical Property of Uridine, 2',3'-didehydro-2',3'-dideoxy-, 5'-benzoate

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Uridine, 2',3'-didehydro-2',3'-dideoxy-, 5'-benzoate

There total 12 articles about Uridine, 2',3'-didehydro-2',3'-dideoxy-, 5'-benzoate 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: 92.0%

C23H19IN2O7 (196867-33-1) → 1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl)uracil (6038-56-8)

Guidance literature:

With sodium hydrogensulfide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.11.087

Reference yield: 90.0%

1-(5-O-benzoyl-2,3-dichloro-2,3-didesoxy-β-D-ribofuranosyl)uracile (74658-82-5) → 1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl)uracil (6038-56-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 2h; Heating;

DOI:10.1016/S0008-6215(00)85518-4

Reference yield: 85.0%

benzoyl chloride (98-88-4) + 2',3'-dideoxy-2',3'-didehydrouridine (5974-93-6) → 1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl)uracil (6038-56-8)

Guidance literature:

With pyridine; at 0 ℃; for 24h;

DOI:10.1021/jm00163a043

upstream raw materials:

benzoyl chloride

2',3'-dideoxy-2',3'-didehydrouridine

Benzoic acid (2R,3S)-3-benzenesulfinyl-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

1-(5-O-benzoyl-2,3-dichloro-2,3-didesoxy-β-D-ribofuranosyl)uracile

Downstream raw materials:

2',3'-dideoxy-4-thio-uridine

2',3'-didehydro-2',3'-dideoxy-4-thiouridine

5-{4-[(2-((5-bromo-2-pyridinyl)aminothiocarbonylamino)-ethyl)-4-methoxyphenoxy]but-1-ynyl}-5'-O-benzoyl-2',3'-didehydro-2',3'-dideoxyuridine

5-{4-[2-(2-(tert-butoxycarbonylamino)ethyl)-4-methoxyphenoxy]but-1-ynyl}-5'-O-benzoyl-2',3'-didehydro-2',3'-dideoxyuridine

Refernces

• 1、 Sheng, Jia,Hassan, Abdalla E. A.,Huang, Zhen. "New telluride-mediated elimination for novel synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides". . p. 3725 - 3729. Retrieved 2008/09/20.
• 2、 Kawakami, Hiroshi,Ebata, Takashi,Koseki, Koshi,Matsumoto, Katsuya,Matsushita, Hajime,et al.. "SYNTHESIS OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES UTILIZING COUPLING REACTIONS BETWEEN NUCLEIC BASES AND PHENYLTHIOSUBSTITUTED 2,3-DIDEOXYRIBOSE". . p. 2451 - 2470. Retrieved 2007/10/02.