Abstract
(Chemical Equation Presented) High mannose glycans composed of α (1→2) and α (1→6) branched sugars are important components of the HIV-associated envelope glycoprotein, gp120. These substructures can be efficiently prepared in solution from glycosyl iodide precursors requiring only a slight excess of the iodide donor, which offers advantages over solid-phase methods that require more than 5 equiv of donor. During the reaction, excess iodide is converted to a glycal that is not easily separated from the desired disaccharide. To overcome this difficulty, a phase-trafficking methodology that relies upon nucleophilic interception of the 1,2 anhydrosugar resulting from oxidation of the glycal has been developed.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 2387-2390 |
| Number of pages | 4 |
| Journal | Journal of Organic Chemistry |
| Volume | 70 |
| Issue number | 6 |
| DOIs | |
| State | Published - Mar 18 2005 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Glycal scavenging in the synthesis of disaccharides using mannosyl iodide donors. / Lam, Son N.; Gervay-Hague, Jacquelyn.
In: Journal of Organic Chemistry, Vol. 70, No. 6, 18.03.2005, p. 2387-2390.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Glycal scavenging in the synthesis of disaccharides using mannosyl iodide donors
AU - Lam, Son N.
AU - Gervay-Hague, Jacquelyn
PY - 2005/3/18
Y1 - 2005/3/18
N2 - (Chemical Equation Presented) High mannose glycans composed of α (1→2) and α (1→6) branched sugars are important components of the HIV-associated envelope glycoprotein, gp120. These substructures can be efficiently prepared in solution from glycosyl iodide precursors requiring only a slight excess of the iodide donor, which offers advantages over solid-phase methods that require more than 5 equiv of donor. During the reaction, excess iodide is converted to a glycal that is not easily separated from the desired disaccharide. To overcome this difficulty, a phase-trafficking methodology that relies upon nucleophilic interception of the 1,2 anhydrosugar resulting from oxidation of the glycal has been developed.
AB - (Chemical Equation Presented) High mannose glycans composed of α (1→2) and α (1→6) branched sugars are important components of the HIV-associated envelope glycoprotein, gp120. These substructures can be efficiently prepared in solution from glycosyl iodide precursors requiring only a slight excess of the iodide donor, which offers advantages over solid-phase methods that require more than 5 equiv of donor. During the reaction, excess iodide is converted to a glycal that is not easily separated from the desired disaccharide. To overcome this difficulty, a phase-trafficking methodology that relies upon nucleophilic interception of the 1,2 anhydrosugar resulting from oxidation of the glycal has been developed.
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UR - http://www.scopus.com/inward/citedby.url?scp=15444376696&partnerID=8YFLogxK
U2 - 10.1021/jo0478609
DO - 10.1021/jo0478609
M3 - Article
C2 - 15760239
AN - SCOPUS:15444376696
VL - 70
SP - 2387
EP - 2390
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 6
ER -