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Synthesis of Two Natural Oleanolic Acid Saponins
Author(s) -
Li ChunXia,
Zang Jing,
Wang Peng,
Zhang XiuLi,
Guan HuaShi,
Li YingXia
Publication year - 2006
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200690098
Subject(s) - chemistry , oleanolic acid , saponin , stereochemistry , residue (chemistry) , natural product , organic chemistry , medicine , alternative medicine , pathology
3‐ O ‐[ β ‐ D ‐Glucopyranosyl‐(1→3)‐ α ‐ L ‐arabinopyranosyl]‐oleanolic acid‐28‐ O ‐[ β ‐ D ‐glucopyranosyl] ester 1 was synthesized concisely by a convergent strategy. Using stepwise fashion for the synthesis of saponin 2 , 3‐ O ‐{[ β ‐ D ‐glucopyranosyl‐(1→2)]‐[ α ‐ L ‐arabinopyranosyl‐(1→3)]‐ α ‐ L ‐arabinopyranosyl}‐oleanolic acid‐28‐ O ‐( β ‐ D ‐glucopyranosyl) ester, an abnormal phenomenon, that the terminal arabinosyl residue took the 1 C 4 conformation instead of typical 4 C 1 form, was observed. Deprotection or heating could not resume the normal conformation, which resulted in the product of 2 ′ not 2 .