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ChemicalBook CAS DataBase List 2',3',5'-Tri-O-acetyluridine
4105-38-8

2',3',5'-Tri-O-acetyluridine synthesis

12synthesis methods
Uridine triacetate is a drug used in the treatment of hereditary orotic aciduria and to treat patients following an overdose of chemotherapy drugs 5-fluorouracil or capecitabine, or in patients exhibiting early-onset, severe or life-threatening toxicity affecting the cardiac or central nervous system, and/or early-onset, unusually severe adverse reactions (e.g., gastrointestinal toxicity and/or neutropenia) within 96 hours following the end of 5-fluorouracil or capecitabine administration. Uridine triacetate was granted breakthrough therapy designation by FDA in 2015. Uridine triacetate is a prodrug of uridine. Synthetic Description Reference: Zhou, X. X.; Welch, C. J.; Chattopadhyaya, J. Pyridyl groups for protection of the imide functions of uridine and guanosine. Exploration of their displacement reactions for site-specific modifications of uracil and guanine bases. Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry. Volume B40. Issue 10. Pages 806-16. Journal. (1986). Synthetic Description Liu, Guang-jian; Zhang, Xiao-tai; Xing, Guo-wen. A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor. Chemical Communications. Volume 51. Issue 64. Pages 12803-12806. Journal; Online Computer File. (2015) Synthetic Description Reference: Zhang, Qingju; Sun, Jiansong; Zhu, Yugen; Zhang, Fuyi; Yu, Biao. An Efficient Approach to the Synthesis of Nucleosides: Gold(I)-Catalyzed N-Glycosylation of Pyrimidines and Purines with Glycosyl ortho-Alkynyl Benzoates. Angewandte Chemie, International Edition. Volume 50. Issue 21. Pages 4933-4936, S4933/1-S4933/101. Journal. (2011)
Synthetic Routes
  • ROUTE 1

    • 202112076755181397.jpg

    Reference: Zhou, X. X.; Welch, C. J.; Chattopadhyaya, J. Pyridyl groups for protection of the imide functions of uridine and guanosine. Exploration of their displacement reactions for site-specific modifications of uracil and guanine bases. Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry. Volume B40. Issue 10. Pages 806-16. Journal. (1986).

  • ROUTE 2

    • 202112075987836098.jpg

    Liu, Guang-jian; Zhang, Xiao-tai; Xing, Guo-wen. A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor. Chemical Communications. Volume 51. Issue 64. Pages 12803-12806. Journal; Online Computer File. (2015)

  • ROUTE 3

    • 202112075765479816.jpg

    Reference: Zhang, Qingju; Sun, Jiansong; Zhu, Yugen; Zhang, Fuyi; Yu, Biao. An Efficient Approach to the Synthesis of Nucleosides: Gold(I)-Catalyzed N-Glycosylation of Pyrimidines and Purines with Glycosyl ortho-Alkynyl Benzoates. Angewandte Chemie, International Edition. Volume 50. Issue 21. Pages 4933-4936, S4933/1-S4933/101. Journal. (2011)

  • ROUTE 4

    • 202112079392169058.jpg

    Chen, Chien-Tien; Kuo, Jen-Huang; Pawar, Vijay D.; Munot, Yogesh S.; Weng, Shieu-Shien; Ku, Cheng-Hsiu; Liu, Cheng-Yuan. Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species. Journal of Organic Chemistry. Volume 70. Issue 4. Pages 1188-1197. 2005.

  • ROUTE 5

    • 202112079283439889.jpg

    Takuma, Yuki; Endo, Kyoko; Murakami, Takeshi; Maeda, Tomoko; Sasaki, Tomoko; Matsumoto, Youichi. Process for preparing nucleosides via condensation reaction of heterocyclic compdounds with pentoses in the presence of iron halide. Assignee Mitsubishi Chemical Corporation, Japan. EP 1334978 A1. (2003).

202112076755181397.jpg

Reference: Zhou, X. X.; Welch, C. J.; Chattopadhyaya, J. Pyridyl groups for protection of the imide functions of uridine and guanosine. Exploration of their displacement reactions for site-specific modifications of uracil and guanine bases. Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry. Volume B40. Issue 10. Pages 806-16. Journal. (1986).

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Yield:4105-38-8 74%

Reaction Conditions:

with sodium hydroxide in water at 20; pH=8; for 4 h;

Steps:

General Nucleoside Acetylation Protocol

General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.

References:

Fernández-García, Christian;Powner, Matthew W. [Synlett,2017,vol. 28,# 1,art. no. ST-2016-S0507-C,p. 78 - 83] Location in patent:supporting information

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