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

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

12synthesis methods

Product Name:2',3',5'-Tri-O-acetyluridine
CAS Number:4105-38-8
Molecular formula:C15H18N2O9
Molecular Weight:370.31

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

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

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).

2466-76-4
355 suppliers
$13.00/5g

58-96-8 Synthesis

58-96-8
631 suppliers
$5.00/1g

4105-38-8
255 suppliers
$7.00/1g

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

108-24-7
5 suppliers
$14.00/250ML

58-96-8 Synthesis

58-96-8
631 suppliers
$5.00/1g

4105-38-8
255 suppliers
$7.00/1g

References

66-22-8 Synthesis

66-22-8
766 suppliers
$5.00/10g

13035-61-5 Synthesis

beta-D-Ribofuranose 1,2,3,5-tetraacetate

13035-61-5
547 suppliers
$5.00/25g

4105-38-8
255 suppliers
$7.00/1g

References

55003-25-3 Synthesis

55003-25-3
15 suppliers
inquiry

4105-38-8
255 suppliers
$7.00/1g

References

D-Ribofuranosyl chloride, 2,3,5-triacetate

40554-98-1
3 suppliers
inquiry

10457-14-4
71 suppliers
$65.00/10mg

4105-38-8
255 suppliers
$7.00/1g

References

2',3',5'-Tri-O-acetyluridine Related Search:

Trifluridine Sodium triacetoxyborohydride Floxuridine 1-beta-D-Arabinofuranosyluracil 2',3',5'-Triacetylguanosine Uracil Uridine 2'-Deoxyuridine 2'-O-Methyluridine 1-(2'-HYDROXYETHYL)URACIL