Abstract
The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and acceptors for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.
| Original language | English |
|---|---|
| Pages (from-to) | 864-877 |
| Number of pages | 14 |
| Journal | Journal of Organic Chemistry |
| Volume | 59 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - Feb 1 1994 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Organic Chemistry
Cite this
Glycosyl Phosphites as Glycosylation Reagents : Scope and Mechanism. / Kondo, Hirosato; Aoki, Shin; Ichikawa, Yoshitaka; Halcomb, Randall L.; Ritzen, Helena; Wong, Chi Huey.
In: Journal of Organic Chemistry, Vol. 59, No. 4, 01.02.1994, p. 864-877.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Glycosyl Phosphites as Glycosylation Reagents
T2 - Scope and Mechanism
AU - Kondo, Hirosato
AU - Aoki, Shin
AU - Ichikawa, Yoshitaka
AU - Halcomb, Randall L.
AU - Ritzen, Helena
AU - Wong, Chi Huey
PY - 1994/2/1
Y1 - 1994/2/1
N2 - The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and acceptors for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.
AB - The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and acceptors for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.
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UR - http://www.scopus.com/inward/citedby.url?scp=33751157840&partnerID=8YFLogxK
U2 - 10.1021/jo00083a032
DO - 10.1021/jo00083a032
M3 - Article
AN - SCOPUS:33751157840
VL - 59
SP - 864
EP - 877
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 4
ER -