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Synthesis of a Trisaccharide Related to the Cytotoxic Triterpenoid Saponins Isolated from the Bark of Albizia procera
Author(s) -
Liu QingChao,
Guo TianTian,
Zhao Cong,
Sun Jing,
Li WenHong
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300195
Subject(s) - chemistry , trisaccharide , glycoconjugate , aglycone , stereochemistry , bark (sound) , glycoside , saponin , biochemistry , physics , acoustics , medicine , alternative medicine , pathology
Chemical synthesis of a trisaccharide related to the cytotoxic triterpenoid saponins isolated from the bark of Albizia procera has been accomplished through a concise stepwise glycosylation strategy starting from commercially available D ‐xylose, 2‐acetamido‐2‐deoxy‐ D ‐glucose and L ‐arabinose. The target trisaccharide was designed with a 4‐methoxyphenyl (MP) aglycone to extend the scope of conversion to suitable glycoconjugates via selective removal of 4‐methoxyphenyl (MP) group. An unexpected phenomenon, i.e. , the arabinosyl residue assumed the 1 C 4 conformation instead of the typical 4 C 1 form, was observed. Deprotection could restore the normal conformation.