Opening book details…
Can I read Oxidation-reduction Sequence for the Synthesis of Peracylated Fluorodeoxy Pentofuranosides on EtoBox?
Oxidation-reduction Sequence for the Synthesis of Peracylated Fluorodeoxy Pentofuranosides by Igor A. Mikhailopulo; Grigorii G. Sivets; Nicolai E. Poopeiko; Natalia B. Khripach is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.
What is Oxidation-reduction Sequence for the Synthesis of Peracylated Fluorodeoxy Pentofuranosides about?
The oxidation of methyl 5-O-benzyl-3(2)-deoxy-3(2)-fluoro-a-D-pentofuranosides with dimethyl sulfoxide-acetic (trifluoroacetic) anhydride was accompanied by epimerization at the carbon atom bearing a fluoro function, resulting in the formation of the corresponding 2-or 3-keto derivatives as mixtures of two epimers in high combined yield. Reduction of a mixture of the erythro/threo epimeric 2-keto sugars (isolated as stable hydrates) with sodium borohydride in benzene-ethanol proceeded stereoselectively leading to the formation of 3-deoxy-3-fluoro riboand lyxo-furanosides, respectively. In the case of the ribo and arabino epimers of the 3-keto sugar (isolated as free ketones), reduction stereoselectivity of the former was > 95% for the 2-deoxy-2-fluoro ribo sugar, whereas a ca. 3:1 lyxo/arabino ratio of products was obtained for the latter. Treatment of a mixture of the 2-epimeric 3-keto sugars with triethylamine in carbon tetrachloride at room temperature for 3-5 h afforded the 2-deoxy-2-fluoro ribo ketone (ca. 9(1%) The synthesis of 1- O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-fluoro-a,[3-D-lyxofuranose (8) and 1-Oacetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoro-J3-D-ribofuranose ( 16) and thei
Who reads Oxidation-reduction Sequence for the Synthesis of Peracylated Fluorodeoxy Pentofuranosides?
It is typically read by researchers, students, and practitioners in Biochemistry, Genetics and Molecular Biology.
- Author
- Igor A. Mikhailopulo; Grigorii G. Sivets; Nicolai E. Poopeiko; Natalia B. Khripach
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)
- Published
- 1995
- Language
- EN
- Field
- Biochemistry, Genetics and Molecular Biology (Life Sciences)