Abstract
The glycosylations of glycals and alcohols using N-iodosuccinimide (NIS) and a catalytic amount of PPh3 effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodoglycosylations with PPh3 significantly increased in comparison to that using NIS alone as an activator. In addition, the glycosylations of glycals and alcohols using catalytic amounts of NIS and P(OPh)3 were effectively realized to give the corresponding 2-deoxyglycosides in high yields.
| Original language | English |
|---|---|
| Pages (from-to) | 9552-9562 |
| Number of pages | 11 |
| Journal | Journal of Organic Chemistry |
| Volume | 80 |
| Issue number | 19 |
| DOIs | |
| Publication status | Published - 2015 Oct 2 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides. / Kimura, Tomoya; Takahashi, Daisuke; Toshima, Kazunobu.
In: Journal of Organic Chemistry, Vol. 80, No. 19, 02.10.2015, p. 9552-9562.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides
AU - Kimura, Tomoya
AU - Takahashi, Daisuke
AU - Toshima, Kazunobu
PY - 2015/10/2
Y1 - 2015/10/2
N2 - The glycosylations of glycals and alcohols using N-iodosuccinimide (NIS) and a catalytic amount of PPh3 effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodoglycosylations with PPh3 significantly increased in comparison to that using NIS alone as an activator. In addition, the glycosylations of glycals and alcohols using catalytic amounts of NIS and P(OPh)3 were effectively realized to give the corresponding 2-deoxyglycosides in high yields.
AB - The glycosylations of glycals and alcohols using N-iodosuccinimide (NIS) and a catalytic amount of PPh3 effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodoglycosylations with PPh3 significantly increased in comparison to that using NIS alone as an activator. In addition, the glycosylations of glycals and alcohols using catalytic amounts of NIS and P(OPh)3 were effectively realized to give the corresponding 2-deoxyglycosides in high yields.
UR - http://www.scopus.com/inward/record.url?scp=84942928891&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84942928891&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b01542
DO - 10.1021/acs.joc.5b01542
M3 - Article
AN - SCOPUS:84942928891
VL - 80
SP - 9552
EP - 9562
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 19
ER -