Synthesis of Thromboxane A 2  Models from Glucose. II. Epoxidation Studies of Hex‐2‐enopyranosides | Zendy

Cirelli Alicia Fernández | Zendy; Moradei Oscar | Zendy; Thiem Joachim | Zendy

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Synthesis of Thromboxane A 2 Models from Glucose. II. Epoxidation Studies of Hex‐2‐enopyranosides

Author(s) -

Cirelli Alicia Fernández,

Moradei Oscar,

Thiem Joachim

Publication year - 1997

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199719970926

Subject(s) - chemistry , moiety , olefin fiber , organic chemistry , stereochemistry , claisen rearrangement , catalysis

The synthesis of halohydrin 7 , a potential precursor of the heterocyclic moiety of thromboxane A 2 (TXA 2 ) is described. Claisen‐Meerwein‐Eschenmoser rearrangement of hex‐3‐enopyranosides 4 and 8 yields the branched olefin sugars 5 and 9 . Epoxidation studies with perbenzimidic acid (Payne's method) and m ‐chloroperbenzoic acid (Anderson's method) were performed. Under treatment of the 2,3‐anhydrosugar 6 with LiBr, the epimeric halohydrins 7 and 10 were obtained in a ratio of 3:2.

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