Flexible Stereo‐ and Regioselective Synthesis of myo‐Inositol Phosphates(Part 1): Via Symmetrical Conduritol B Derivatives

Abstract

A practical route is described for the preparation of myo-inositol polyphosphates. Optically pure myo-inositol derivatives can be prepared from p-benzoquinone in both forms by enzymatic resolution of a C 2 -symmetric diacetoxyconduritol B key intermediate, followed by cis-dihydroxylation. Selective

Synthesis of Unsymmetric Diphospho‐Inositol Polyphosphates

“…The other diastereomer 10 was purified to a ratio 98:2 by normal flash column chromatography (FC). The regioselectivity was assigned by cleavage of the protecting groups giving the enantiomeric inositol‐1‐phosphate or inositol‐3‐phosphate for which the optical rotations are known (see Supporting Information) 8d…”

Contribution of Phosphates and Adenine to the Potency of Adenophostins at the IP3 Receptor: Synthesis of All Possible Bisphosphates of Adenophostin A

“… 39 −10 ( c 1, H 2 O, tetrapotassium salt); Lit. 53 −4.4 ( c 0.3, H 2 O, pH 6); Lit. 53 +7.9 ( c 1.2, H 2 O, free acid).…”

“… 53 −4.4 ( c 0.3, H 2 O, pH 6); Lit. 53 +7.9 ( c 1.2, H 2 O, free acid). 1 H NMR (500 MHz, TEA + salt, D 2 O): 3.60 (dd, 1H, 10.0 Hz, 2.8 Hz, H-1), 3.70 (dd, 1H, 9.8 Hz, 2.8 Hz, H-3), 3.81 (dd, 1H, 9.7 Hz, 9.5 Hz, H-6), 3.99 (ddd, 9.0 Hz, 9.0 Hz, 9.0 Hz, H-5), 4.07 (dd, 1H, 2.8 Hz, 2.8 Hz, H-2), 4.27 (dd, 1H, 9.3 Hz, 9.2 Hz, 9.2 Hz, H-4).…”

Flexible Stereo‐ and Regioselective Synthesis of myo‐Inositol Phosphates(Part 2): Via Nonsymmetrical Conduritol B Derivatives

“…In this paper, we present an extension to this concept that leads to even greater flexibility. As reported previously, [19] the syntheses of myo-inositol phosphates via C 2 -symmetric conduritol B derivatives leads to pairwise protected (differentiated) myo-inositol intermediates, and this limits the number of possible myoinositol phosphates. Breaking the C 2 symmetry of the conduritol B precursors makes additional substitution patterns available; we used this approach already to synthesize azido-and amino-myo-inositols.…”

“…www.eurjoc.org but these isomers are prepared more effectively by the symmetric concept, as reported earlier. [19] Outlook It should be noted that this concept is not limited to the protecting pattern described above. It is possible to differentiate within the triol unit in monobenzylconduritol B (8) by isopropylidene protection: only the 2,3-O-isopropylideneconduritol B derivative 30 is obtained, in 80 % yield (Scheme 10).…”