Abstract
β-Stereoselective mannosylations were conducted using a 1,2-anhydromannose donor and mono-ol acceptors in the presence of a glycosyl-acceptor-derived borinic ester. Reactions proceeded smoothly under mild conditions to provide the corresponding β-mannosides with high stereoselectivity in moderate to high yields. In addition, the present glycosylation method was applied successfully to the total synthesis of acremomannolipin A.
| Original language | English |
|---|---|
| Pages (from-to) | 2288-2291 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 18 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2016 May 6 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
Cite this
Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor. / Tanaka, Masamichi; Nashida, Junki; Takahashi, Daisuke; Toshima, Kazunobu.
In: Organic Letters, Vol. 18, No. 9, 06.05.2016, p. 2288-2291.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor
AU - Tanaka, Masamichi
AU - Nashida, Junki
AU - Takahashi, Daisuke
AU - Toshima, Kazunobu
PY - 2016/5/6
Y1 - 2016/5/6
N2 - β-Stereoselective mannosylations were conducted using a 1,2-anhydromannose donor and mono-ol acceptors in the presence of a glycosyl-acceptor-derived borinic ester. Reactions proceeded smoothly under mild conditions to provide the corresponding β-mannosides with high stereoselectivity in moderate to high yields. In addition, the present glycosylation method was applied successfully to the total synthesis of acremomannolipin A.
AB - β-Stereoselective mannosylations were conducted using a 1,2-anhydromannose donor and mono-ol acceptors in the presence of a glycosyl-acceptor-derived borinic ester. Reactions proceeded smoothly under mild conditions to provide the corresponding β-mannosides with high stereoselectivity in moderate to high yields. In addition, the present glycosylation method was applied successfully to the total synthesis of acremomannolipin A.
UR - http://www.scopus.com/inward/record.url?scp=84969610589&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84969610589&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.6b00926
DO - 10.1021/acs.orglett.6b00926
M3 - Article
AN - SCOPUS:84969610589
VL - 18
SP - 2288
EP - 2291
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 9
ER -