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
Hauptverfasser: Shinotsuka, Yuta, Nakajima, Riko, Ogawa, Kohei, Takise, Kaede, Takeuchi, Yutaka, Tanaka, Hiroshi, Sasaki, Kaname
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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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00139g