Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides
Crich, D; Banerjee, A
| HERO ID | 5415259 |
|---|---|
| In Press | No |
| Year | 2006 |
| Title | Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides |
| Authors | Crich, D; Banerjee, A |
| Journal | Journal of the American Chemical Society |
| Volume | 128 |
| Issue | 24 |
| Page Numbers | 8078-8086 |
| Abstract | The synthesis of d- and l-glycero-alpha-manno-thioheptopyranosides, protected with 4,6-O-alkylidene-type acetals is described. In glycosylations carried out with preactivation with the 1-benzenesulfinylpiperidine/trifluoromethanesulfonic anhydride couple, both the D- and L-glycero series exhibit excellent beta-selectivity with a range of glycosyl acceptors. In contrast, a 4,7-O-alkylidene acetal was found not to afford beta-selectivity. With a 4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetal protected thioglycoside, excellent beta-selectivity was obtained in glycosylation reactions, and subsequent treatment with tributyltin hydride and azoisobutyronitrile brought about clean fragmentation to the 6-deoxy-glycero-beta-D-manno-heptopyranosides. This chemistry was applied to the stereocontrolled synthesis of methyl alpha-L-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl-(1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L-rhamno-pyranoside, a component of the lipopolysaccharide from Plesimonas shigelloides. |
| Doi | 10.1021/ja061594u |
| Pmid | 16771524 |
| Wosid | WOS:000238258000065 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |