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. 2024 Mar 27;22(13):2544-2548.
doi: 10.1039/d4ob00139g.

Stereoselective synthesis of D- glycero-D- manno-heptose-1β,7-bisphosphate (HBP) from D-mannurono-2,6-lactone

Yuta Shinotsuka  1 , Riko Nakajima  1 , Kohei Ogawa  1 , Kaede Takise  1 , Yutaka Takeuchi  2 , Hiroshi Tanaka  2 , Kaname Sasaki  1
Affiliations

Stereoselective synthesis of D- glycero-D- manno-heptose-1β,7-bisphosphate (HBP) from D-mannurono-2,6-lactone

Yuta Shinotsuka et al. Org Biomol Chem. .

Abstract

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.

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