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The synthesis of a series of tetrahydrofuranyl α- and β-xylopyranoside trisphosphates, designed by excision of three motifs of adenophostin A is reported. The synthetic route features improved preparations of allyl α-d-xylopyranoside and its 2-O-benzyl ether, and gives access to four diastereoisomeric trisphosphates, which show a range of abilities to mobilise Ca 2+ from the intracellular...
Epimeric C-glycoside based polyphosphates, α- and β-d-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from d-glucose. The key intermediate, allyl 2,6-di-O-benzyl-α-d-glucopyranoside, was prepared in five steps (67% yield) from allyl α-d-glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P 3 receptors of...
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