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 in | Organic letters Vol. 26; no. 7; pp. 1468 - 1471 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
23.02.2024
Amer Chemical Soc |
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| Abstract | 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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| AbstractList | 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. 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. The branched fructooligosaccharides ABW90-1 and ABW50-1 from with potent antiosteoporosis activities have been synthesized for the first time. The synthetic approach highlights the following features: (1) 6- -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, CH Cl ) 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. 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 beta-d-fructofuranosylation via a hydrogen-bond-mediated aglycone delivery strategy for the highly stereoselective constructions of beta-(2 -> 6)-d-fructofuranosidic linkages and beta-(2 -> 1)-d-fructofuranosidic linkages in the internal positions under the reaction conditions (DBDMH, -20 degrees C, CH2Cl2) and (2) the reaction conditions (DBDMH, -78 degrees C to -35 degrees C, toluene) for highly stereoselective formations of beta-(2 -> 1)-d-fructofuranosidic linkages in the terminal positions. |
| Author | Liu, Bin Wang, Xiufang Xiao, Guozhi Li, Kaifeng |
| AuthorAffiliation | Department of Chemistry University of Chinese Academy of Sciences, Chinese Academy of Sciences State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany |
| AuthorAffiliation_xml | – name: University of Chinese Academy of Sciences, Chinese Academy of Sciences – name: Department of Chemistry – name: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany |
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| Keywords | INULIN CARBOHYDRATE VACCINES CHEMISTRY FRUCTAN STRUCTURAL-CHARACTERIZATION STEREOSPECIFIC SYNTHESIS OLIGOSACCHARIDE GLYCOSYLATION OSTEOPOROSIS POLYSACCHARIDE |
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| Snippet | The branched fructooligosaccharides ABW90-1 and ABW50-1 from Achyranthes bidentata with potent antiosteoporosis activities have been synthesized for the first... The branched fructooligosaccharides ABW90-1 and ABW50-1 from with potent antiosteoporosis activities have been synthesized for the first time. The synthetic... |
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| StartPage | 1468 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Highly Stereoselective Synthesis of Branched Fructooligosaccharides ABW90‑1 and ABW50‑1 from Achyranthes bidentata with Potent Antiosteoporosis Activities |
| URI | http://dx.doi.org/10.1021/acs.orglett.4c00092 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001167184100001 https://www.ncbi.nlm.nih.gov/pubmed/38329784 https://search.proquest.com/docview/2923909060 |
| Volume | 26 |
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