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Stereochemical aspects of the formation of diastereoisomeric 3-acetyl-2-(polyacetoxyalkyl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazoles

✍ Scribed by László Somogyi

Book ID
102994656
Publisher
Elsevier Science
Year
1988
Tongue
English
Weight
738 KB
Volume
182
Category
Article
ISSN
0008-6215

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✦ Synopsis

The synthesis of D-and L-3-acetyl-2-[arabino-(tetra-acetoxybutyl)]-[( -)-and ( + )-4a, ( -)-4b] and 3-acetyl-2-[D-manno-(penta-acetoxypentyl)]-5-phenyl-2,3dihydro-1,3,4-oxadiazoles [( + )-4d] via cyclisation of the corresponding (O-acetylated) aldose benzoylhydrazones (2a,b,d) under acetylating conditions is described. The stereochemical aspects of the formation of C-2 epimeric oxadiazolines [e.g., (-)-and (+)-4a] are discussed on fhe basis of optical rotation and n.m.r. data. The acetylation of methylglyoxal bis(benzoylhydrazone) (8) was found to give diastereoisomeric 1,3,4-oxadiazolines (12a and 12b) instead of the bis(acetylbenzoylhydrazone) 9 claimed in the literature.

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