127446-71-3Relevant academic research and scientific papers
A Ca2+-mobilising carbohydrate-based polyphosphate: Synthesis of 2- hydroxyethyl α-D-glucopyranoside 2',3,4-trisphosphate
Jenkins, David J.,Potter, Barry V.L.
, p. 169 - 182 (2007/10/03)
Two routes to a glucose-based mimic of the second messenger 1D-myo- inositol 1,4,5-trisphosphate related to adenophostin A are described. Fischer glycosidation of D-glucose with allyl alcohol in the presence of a strong cation-exchange resin gave a 7:3 α:β-anomeric mixture of allyl glucopyranosides (5ab) from which the pure α anomer 5a was isolated by crystallisation. Treatment of 5ab with 1.05 equiv of dibutyltin oxide followed by 2.1 equiv of benzoyl chloride gave allyl 2,6-di-O-benzoyl-α-D- glucopyranoside, which was converted in 3 steps into allyl 2,6-di-O-benzyl- 3,4-O-isopropylidene-α-D-glucopyranoside (4). Alternatively, treatment of 5a with 2.5 equiv of dibutyltin oxide followed by benzyl bromide gave allyl 2,6-di-O-benzyl-α-D-glucopyranoside (9) which was also converted into 4. Compound 4 was elaborated to the phosphorylation precursor 2-hydroxyethyl 2,6-di-O-benzyl-α-D-glucopyranoside (12) in a convenient one-pot reaction, and 12 was phosphorylated and deblocked to afford 2-hydroxyethyl α-D- glucopyranoside 2',3.4-trisphosphate. The 2,6-di-O-benzyl derivative 9 was converted in high yield into 2,6-di-O-benzyl-3,4-di-O-(p-methoxybenzyl)-D- glucopyranose, a useful intermediate for the synthesis of adenophostin A and related compounds.
(2-hydroxyethyl)-α-D-glucopyranoside-2',3,4-trisphosphate: Synthesis of a second messenger mimic related to adenophostin A
Jenkins,Potter
, p. 1169 - 1170 (2007/10/02)
A concise synthetic route from D-glucose to a chiral, biologically active, phosphorylated analogue of the highly potent Ca2+-mobilising agonist adenophostin A has been developed, involving a regioselective dibenzylation of allyl α-D-glucopyranoside and a one-pot Lemieux-type allyl oxidation with subsequent reduction and neighbouring deketalisation, to provide the key intermediate for phosphorylation.
Regioselective acylation of carbohydrates with 1-acyloxy-1H-benzotriazoles
Pelyvas,Lindhorst,Streicher,Thiem
, p. 1015 - 1018 (2007/10/02)
Acylation of representative carbohydrate derivatives was accomplished with in situ generated 1-acyloxy-1H-benzotriazoles. The observed high regioselectivity, mild reaction conditions and convenient work-up make the presented one-pot procedure generally applicable and more advantageous than acylations with previously introduced reagents, including N-acylimidazoles.
En Route to Thromboxane Compounds from Carbohydrates, I. Synthesis of the Unsaturated Sugar Precursors
Pelyvas, Istvan,Lindhorst, Thisbe,Thiem, Joachim
, p. 761 - 769 (2007/10/02)
Allyl 4-C-hex-2-enopyranosides 18a-c, representing chiral precursors for the carbohydrate-based construction of the ring systems of thromboxane A2 and B2 were prepared by means of the Claisen-type rearrangement of the suitably substituted hex-3-enopyranosides 7a,b.The latter sugars were synthesized from allyl α-D-glucopyranoside (9) by modification of known procedures, including selective O-benzoylation with 1-(benzoyloxy)-1H-benzotriazole (11), and Tipson-Cohen sulfonyl ester elimination of the 3,4-di-O-mesylates 16 and 17.Studies on the corresponding methyl glycosides 8a-c showed a reduce d stability of the 6-O-(tert-butyldiphenylsilyl) ether group under the Tipson-Cohen reaction conditions.
