Highly Stereoselective Synthesis of Branched Fructooligosaccharides ABW90‑1 and ABW50‑1 from Achyranthes bidentata with Potent Antiosteoporosis Activities

The branched fructooligosaccharides ABW90-1 and ABW50-1 from Achyranthes bidentata with potent antiosteoporosis activities have been synthesized for the first time. The synthetic approach highlights the following features: (1) 6-O-picoloyl-directed β-d-fructofuranosylation via a hydrogen-bond-mediat...

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Published inOrganic letters Vol. 26; no. 7; pp. 1468 - 1471
Main Authors Li, Kaifeng, Liu, Bin, Wang, Xiufang, Xiao, Guozhi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.02.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
INULIN
CARBOHYDRATE VACCINES
CHEMISTRY
FRUCTAN
STRUCTURAL-CHARACTERIZATION
STEREOSPECIFIC SYNTHESIS
OLIGOSACCHARIDE
GLYCOSYLATION
OSTEOPOROSIS
POLYSACCHARIDE
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Summary:The branched fructooligosaccharides ABW90-1 and ABW50-1 from Achyranthes bidentata with potent antiosteoporosis activities have been synthesized for the first time. The synthetic approach highlights the following features: (1) 6-O-picoloyl-directed β-d-fructofuranosylation via a hydrogen-bond-mediated aglycone delivery strategy for the highly stereoselective constructions of β-(2 → 6)-d-fructofuranosidic linkages and β-(2 → 1)-d-fructofuranosidic linkages in the internal positions under the reaction conditions (DBDMH, −20 °C, CH2Cl2) and (2) the reaction conditions (DBDMH, −78 °C to −35 °C, toluene) for highly stereoselective formations of β-(2 → 1)-d-fructofuranosidic linkages in the terminal positions.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00092