Synthesis of the tetrasaccharide alpha-D-Glcp(1 -> 3)-alpha-D-Manp-(1 -> 2)-alpha-D-Manp-(1 -> 2)-alpha-D-Manp recognized by calreticulin/calnexin
Research output: Contribution to journal › Article › peer-review
Electronic versions
DOI
The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-α-d-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-α-d-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete α-selectivity, a disaccharide building block in high yield. The perbenzylated derivative of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known methyl dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compound in 47% overall yield.
Keywords
- Calreticulin substrates, Iodide glycosyl donors, Triphenylphosphine oxide promotion, Thioglycoside block donor
| Original language | English |
|---|---|
| Pages (from-to) | 2558-2562 |
| Journal | Carbohydrate Research |
| Volume | 340 |
| Issue number | 16 |
| DOIs | |
| Publication status | Published - 21 Nov 2005 |
| Externally published | Yes |