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O-Regioselective Synthesis with the Silver Salt Method.

Yi-Gui Wang1, Ericka C Barnes1

  • 1Department of Chemistry, Southern CT State University, 501 Crescent Street, New Haven, Connecticut 06515, United States.

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|August 29, 2019
PubMed
Summary
This summary is machine-generated.

Computational studies reveal that the silver salt method provides excellent O-regioselectivity in glycosidation reactions with 5-fluorouracil (5-FU) derivatives. This selectivity is attributed to favorable ionic and covalent interactions in transition states, explained by the hard and soft acids and bases principle.

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Area of Science:

  • Computational Chemistry
  • Organic Synthesis
  • Medicinal Chemistry

Background:

  • The silver salt method is frequently used for glycosidation reactions.
  • Ambident nucleophiles, such as 5-fluorouracil (5-FU) derivatives, can react at multiple sites, leading to regioselectivity challenges.
  • Understanding the factors governing regioselectivity is crucial for optimizing synthetic strategies.

Purpose of the Study:

  • To computationally investigate the O-regioselectivity of glycosidation reactions involving 2-O-substituted 5-fluorouracil (5-FU) using the silver salt method.
  • To elucidate the underlying electronic and steric factors that dictate the preferential O-glycosidation over N-glycosidation.
  • To compare the reaction pathways with and without silver-bromide ion interaction in the transition states.

Main Methods:

  • Density Functional Theory (DFT) calculations using the B3LYP/6-31+G(d):DZP level of theory.
  • High-level ab initio calculations (MP2/6-311++G(2d,p):DZP) were employed for key transition states.
  • Analysis of reaction pathways involving 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-α-d-glucopyranose and silver salts of 5-FU derivatives.

Main Results:

  • Calculations consistently showed significantly lower activation energy barriers for O-glycosidation compared to N-glycosidation (13.3–22.2 kcal/mol).
  • The pathway involving silver-bromide ion interaction in transition states exhibited lower activation barriers than the non-interacting pathway.
  • Favorable ionic (C+···O-) and covalent (Ag···N) interactions in O-reaction transition states were identified, aligning with the hard and soft acids and bases principle.

Conclusions:

  • The excellent O-regioselectivity observed in the silver salt method for 5-FU derivatives is computationally validated.
  • The interaction between silver and bromide ions, along with favorable ionic and covalent interactions involving the ambident nucleophile, drives the observed selectivity.
  • These findings provide a theoretical basis for the efficient synthesis of O-glycosylated 5-FU derivatives.