Abstract
Regioselective and 1,2-cis-α-stereoselective glycosylations using 1α,2α-anhydro glycosyl donors and diol glycosyl acceptors in the presence of a glycosyl-acceptor-derived boronic ester catalyst. The reactions proceed smoothly to give the corresponding 1,2-cis-α-glycosides with high stereo- and regioselectivities in high yields without any further additives under mild reaction conditions. In addition, the present glycosylation method was successfully applied to the synthesis of an isoflavone glycoside.
| Original language | English |
|---|---|
| Pages (from-to) | 10935-10939 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 54 |
| Issue number | 37 |
| DOIs | |
| Publication status | Published - 2015 Sep 1 |
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Keywords
- boron
- glycosylation
- regioselectivity
- stereoselectivity
- synthetic methods
ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
Cite this
Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst. / Nakagawa, Akira; Tanaka, Masamichi; Hanamura, Shun; Takahashi, Daisuke; Toshima, Kazunobu.
In: Angewandte Chemie - International Edition, Vol. 54, No. 37, 01.09.2015, p. 10935-10939.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst
AU - Nakagawa, Akira
AU - Tanaka, Masamichi
AU - Hanamura, Shun
AU - Takahashi, Daisuke
AU - Toshima, Kazunobu
PY - 2015/9/1
Y1 - 2015/9/1
N2 - Regioselective and 1,2-cis-α-stereoselective glycosylations using 1α,2α-anhydro glycosyl donors and diol glycosyl acceptors in the presence of a glycosyl-acceptor-derived boronic ester catalyst. The reactions proceed smoothly to give the corresponding 1,2-cis-α-glycosides with high stereo- and regioselectivities in high yields without any further additives under mild reaction conditions. In addition, the present glycosylation method was successfully applied to the synthesis of an isoflavone glycoside.
AB - Regioselective and 1,2-cis-α-stereoselective glycosylations using 1α,2α-anhydro glycosyl donors and diol glycosyl acceptors in the presence of a glycosyl-acceptor-derived boronic ester catalyst. The reactions proceed smoothly to give the corresponding 1,2-cis-α-glycosides with high stereo- and regioselectivities in high yields without any further additives under mild reaction conditions. In addition, the present glycosylation method was successfully applied to the synthesis of an isoflavone glycoside.
KW - boron
KW - glycosylation
KW - regioselectivity
KW - stereoselectivity
KW - synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=84940688656&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84940688656&partnerID=8YFLogxK
U2 - 10.1002/anie.201504182
DO - 10.1002/anie.201504182
M3 - Article
C2 - 26205146
AN - SCOPUS:84940688656
VL - 54
SP - 10935
EP - 10939
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 37
ER -