Abstract
Glycosyl iodides have been prepared and subjected to glycosylation under neutral conditions. The reactions are highly efficient, giving α glycosides even with sterically demanding glycosyl acceptors. Glucosyl iodides react with allyl alcohol slowest and require refluxing conditions. Galactosyl iodides are intermediate in reactivity, providing the allyl glycoside in 3 h at room temperature, whereas glycosylation of fucosyl iodides occurs in less than 1 h under similar conditions. The scope and limitations of the reactions were demonstrated with a variety of acceptors, including an anomeric hydroxyl group, to give trehalose analogs. β-Selective glycosylation of glucosyl iodides, in the absence of C-2 participation, could be achieved by simply changing the solvent from benzene to acetonitrile. Copyright (C) 1999 Elsevier Science Ltd.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 61-69 |
| Number of pages | 9 |
| Journal | Carbohydrate Research |
| Volume | 320 |
| Issue number | 1-2 |
| DOIs | |
| State | Published - Jul 20 1999 |
| Externally published | Yes |
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Keywords
- Glycosyl bromide
- Glycosyl iodide
- Halide-catalyzed anomerization
- In situ anomerization
- Trehalose analogs
- α-Glycosylation
ASJC Scopus subject areas
- Biochemistry
- Molecular Biology
- Organic Chemistry
Cite this
Glycosyl iodides are highly efficient donors under neutral conditions. / Hadd, Michael J.; Gervay-Hague, Jacquelyn.
In: Carbohydrate Research, Vol. 320, No. 1-2, 20.07.1999, p. 61-69.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Glycosyl iodides are highly efficient donors under neutral conditions
AU - Hadd, Michael J.
AU - Gervay-Hague, Jacquelyn
PY - 1999/7/20
Y1 - 1999/7/20
N2 - Glycosyl iodides have been prepared and subjected to glycosylation under neutral conditions. The reactions are highly efficient, giving α glycosides even with sterically demanding glycosyl acceptors. Glucosyl iodides react with allyl alcohol slowest and require refluxing conditions. Galactosyl iodides are intermediate in reactivity, providing the allyl glycoside in 3 h at room temperature, whereas glycosylation of fucosyl iodides occurs in less than 1 h under similar conditions. The scope and limitations of the reactions were demonstrated with a variety of acceptors, including an anomeric hydroxyl group, to give trehalose analogs. β-Selective glycosylation of glucosyl iodides, in the absence of C-2 participation, could be achieved by simply changing the solvent from benzene to acetonitrile. Copyright (C) 1999 Elsevier Science Ltd.
AB - Glycosyl iodides have been prepared and subjected to glycosylation under neutral conditions. The reactions are highly efficient, giving α glycosides even with sterically demanding glycosyl acceptors. Glucosyl iodides react with allyl alcohol slowest and require refluxing conditions. Galactosyl iodides are intermediate in reactivity, providing the allyl glycoside in 3 h at room temperature, whereas glycosylation of fucosyl iodides occurs in less than 1 h under similar conditions. The scope and limitations of the reactions were demonstrated with a variety of acceptors, including an anomeric hydroxyl group, to give trehalose analogs. β-Selective glycosylation of glucosyl iodides, in the absence of C-2 participation, could be achieved by simply changing the solvent from benzene to acetonitrile. Copyright (C) 1999 Elsevier Science Ltd.
KW - Glycosyl bromide
KW - Glycosyl iodide
KW - Halide-catalyzed anomerization
KW - In situ anomerization
KW - Trehalose analogs
KW - α-Glycosylation
UR - http://www.scopus.com/inward/record.url?scp=0032880786&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0032880786&partnerID=8YFLogxK
U2 - 10.1016/S0008-6215(99)00146-9
DO - 10.1016/S0008-6215(99)00146-9
M3 - Article
VL - 320
SP - 61
EP - 69
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 1-2
ER -