Abstract
Abstract The generation of β-lactosyl iodide was carried out under non-in situ-anomerization, metal free conditions by reacting commercially available β-per-O-acetylated lactose with trimethylsilyl iodide (TMSI). The β-iodide was surprisingly stable as evidenced by NMR spectroscopy. Introduction of octanol or cholesterol under microwave conditions gave high yields of α-linked glycoconjugates. Careful analysis of the reaction products and mechanistic considerations suggest an acid catalyzed rearrangement that provides α-linked glycosylation products with a free C2-hydroxyl. Accessibility to these compounds may further advance glycolipidomic profiling of immune modulating bacterial derived-glycans.
| Original language | English (US) |
|---|---|
| Article number | 46284 |
| Pages (from-to) | 3690-3694 |
| Number of pages | 5 |
| Journal | Tetrahedron Letters |
| Volume | 56 |
| Issue number | 23 |
| DOIs | |
| State | Published - Dec 1 2014 |
Fingerprint
Keywords
- 1,2-cis
- Glycosyl iodide glycosylation
- H. pylori
- Mechanism
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Synthesis of cholesteryl-α-d-lactoside via generation and trapping of a stable β-lactosyl iodide. / Davis, Ryan A.; Fettinger, James C.; Gervay-Hague, Jacquelyn.
In: Tetrahedron Letters, Vol. 56, No. 23, 46284, 01.12.2014, p. 3690-3694.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of cholesteryl-α-d-lactoside via generation and trapping of a stable β-lactosyl iodide
AU - Davis, Ryan A.
AU - Fettinger, James C.
AU - Gervay-Hague, Jacquelyn
PY - 2014/12/1
Y1 - 2014/12/1
N2 - Abstract The generation of β-lactosyl iodide was carried out under non-in situ-anomerization, metal free conditions by reacting commercially available β-per-O-acetylated lactose with trimethylsilyl iodide (TMSI). The β-iodide was surprisingly stable as evidenced by NMR spectroscopy. Introduction of octanol or cholesterol under microwave conditions gave high yields of α-linked glycoconjugates. Careful analysis of the reaction products and mechanistic considerations suggest an acid catalyzed rearrangement that provides α-linked glycosylation products with a free C2-hydroxyl. Accessibility to these compounds may further advance glycolipidomic profiling of immune modulating bacterial derived-glycans.
AB - Abstract The generation of β-lactosyl iodide was carried out under non-in situ-anomerization, metal free conditions by reacting commercially available β-per-O-acetylated lactose with trimethylsilyl iodide (TMSI). The β-iodide was surprisingly stable as evidenced by NMR spectroscopy. Introduction of octanol or cholesterol under microwave conditions gave high yields of α-linked glycoconjugates. Careful analysis of the reaction products and mechanistic considerations suggest an acid catalyzed rearrangement that provides α-linked glycosylation products with a free C2-hydroxyl. Accessibility to these compounds may further advance glycolipidomic profiling of immune modulating bacterial derived-glycans.
KW - 1,2-cis
KW - Glycosyl iodide glycosylation
KW - H. pylori
KW - Mechanism
UR - http://www.scopus.com/inward/record.url?scp=84937757989&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84937757989&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2015.05.012
DO - 10.1016/j.tetlet.2015.05.012
M3 - Article
AN - SCOPUS:84937757989
VL - 56
SP - 3690
EP - 3694
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 23
M1 - 46284
ER -