Stereoselective synthesis of ----heptose-1β,7-bisphosphate (HBP) from -mannurono-2,6-lactone
The synthesis of d - glycero - d - manno -heptose-1β,7-bisphosphate (HBP) from d -mannose is described. This synthetic approach is notable for the elongation of the seventh carbon, employing mannurono-2,6-lactone, the substrate-controlled establishment of the C-6 configuration, and the nucleophilic...
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Veröffentlicht in: | Organic & biomolecular chemistry 2024-03, Vol.22 (13), p.2544-2548 |
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Zusammenfassung: | The synthesis of
d
-
glycero
-
d
-
manno
-heptose-1β,7-bisphosphate (HBP) from
d
-mannose is described. This synthetic approach is notable for the elongation of the seventh carbon, employing mannurono-2,6-lactone, the substrate-controlled establishment of the C-6 configuration, and the nucleophilic introduction of phosphate at the C-1 position through the utilization of 4,6-
O
-benzylidene-α-triflate.
The synthesis of HBP is distinguished by the β-steroselective glycosylation of phosphate and ketone formation from the 2,6-lactone through the utilization of a C1 nucleophile. |
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ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/d4ob00139g |