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Study on the mechanism of diazomethane degradation of the sugar – aglycone linkage in gypsogenin 3‐ O ‐glycoside
Author(s) -
Higuchi Ryuichi,
Tokimitsu Yoshinori,
Komori Tetsuya
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819880312
Subject(s) - aglycone , chemistry , diazomethane , linkage (software) , sugar , glycoside , stereochemistry , degradation (telecommunications) , mechanism (biology) , organic chemistry , biochemistry , telecommunications , philosophy , epistemology , computer science , gene
The mechanism of the diazomethane degradation of the sugar–aglycone linkage of the gypsogenin 3‐ O ‐glycoside ( 1 ) was studied. Since there are three kinds of functional groups in 1 – the 4α‐aldehyde group in the aglycone, the carboxy, and the 4′‐hydroxy group in the glucuronic acid – which are presumed to contribute to the degradation reaction, the role of each functional group was examined using synthesized model compounds. As a result of the study, only the 4α‐aldehyde group was shown to be essential. By taking the above evidence and the reaction of the aldehyde with diazomethane into account, the degradation is thought to proceed through an epoxide intermediate as shown in Scheme 6. The reaction of gypsogenin with diazomethane was also examined.