Abstract
Highly β-stereoselective glycosylations of glycosyl acceptors having a primary hydroxyl group by using a novel glycosyl donor, α-glycosyl 6-nitro-2-benzothiazoate (3), proceeded smoothly in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) in CH2Cl2 at -78°C to afford the corresponding glycosides in high yields. The donor 3 gave β-saccharides more dominantly compared with those using other α-glycosyl donors such as thioform- and trichloroacet-imidates or fluoride under the same conditions.
| Original language | English |
|---|---|
| Pages (from-to) | 340-341 |
| Number of pages | 2 |
| Journal | Chemistry Letters |
| Volume | 32 |
| Issue number | 4 |
| Publication status | Published - Apr 5 2003 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
Cite this
Glycosyl 6-nitro-2-benzothiazoate. A highly efficient donor for β-stereoselective glycosylation. / Mukaiyama, Teruaki; Hashihayata, Takashi; Mandai, Hiroki.
In: Chemistry Letters, Vol. 32, No. 4, 05.04.2003, p. 340-341.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Glycosyl 6-nitro-2-benzothiazoate. A highly efficient donor for β-stereoselective glycosylation
AU - Mukaiyama, Teruaki
AU - Hashihayata, Takashi
AU - Mandai, Hiroki
PY - 2003/4/5
Y1 - 2003/4/5
N2 - Highly β-stereoselective glycosylations of glycosyl acceptors having a primary hydroxyl group by using a novel glycosyl donor, α-glycosyl 6-nitro-2-benzothiazoate (3), proceeded smoothly in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) in CH2Cl2 at -78°C to afford the corresponding glycosides in high yields. The donor 3 gave β-saccharides more dominantly compared with those using other α-glycosyl donors such as thioform- and trichloroacet-imidates or fluoride under the same conditions.
AB - Highly β-stereoselective glycosylations of glycosyl acceptors having a primary hydroxyl group by using a novel glycosyl donor, α-glycosyl 6-nitro-2-benzothiazoate (3), proceeded smoothly in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) in CH2Cl2 at -78°C to afford the corresponding glycosides in high yields. The donor 3 gave β-saccharides more dominantly compared with those using other α-glycosyl donors such as thioform- and trichloroacet-imidates or fluoride under the same conditions.
UR - http://www.scopus.com/inward/record.url?scp=0038600686&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0038600686&partnerID=8YFLogxK
M3 - Article
VL - 32
SP - 340
EP - 341
JO - Chemistry Letters
JF - Chemistry Letters
SN - 0366-7022
IS - 4
ER -