Synthesis of mono- and unsymmetrical bis-orthoesters of scyllo-inositol

Abstract

of sodium azide (20 g, 0.31 mol), ammonium chloride (0.5 g), water (50 mL), and ethanol (150 mL), heated, and stirred under reflux for 16 h. The resulting mixture was evaporated to a residue keeping the heating bath below 40 °C. The residue was suspended in chloroform (500 mL) and washed with saturated brine (2 X 50 mL). The organic layer was evaporated to an oil yielding 4.2 g of crude 16.(l/3,2a,3/3)-3-Amino-l,2-cycIopentanediol Hydrochloride (17). The crude 16 (4.2 g) was dissolved in methanol (150 mL), 10% Pd/C (0.5 g) was added, and the mixture was hydrogenated at 50 psi on a Parr hydrogenator for 2 h. The catalyst was removed by filtration, and the solution was evaporated to an oil. The oil was stirred with 5 M ethanolic HC1 for 16 h and then evaporated to a residue. Crystallization from propan-l-ol yielded 17 (2.8 g, 38%), mp 34-37 °C: IR (Nujol) 3300 cm'1; NMR (Me2SO-d6)

scyllo‐Inositol Pentakisphosphate as an Analogue of myo‐Inositol 1,3,4,5,6‐Pentakisphosphate: Chemical Synthesis, Physicochemistry and Biological Applications

“…Oxidation of 3 at C-2, [21] followed by stereoselective reduction by using sodium borohydride [22] exclusively gave the axial alcohol 5. Interestingly, the fact that 5 has the scyllo-configuration is immediately apparent from the 1 H NMR spectrum, because the signal corresponding to the methylidyne proton appears as a singlet, while in the myo-epimer 3 it appears as a narrow doublet due to a long range 5 J spin-spin coupling to the axial H-2 proton.…”

Characterization and Insulin‐Mimetic Potential of Oxidovanadium(IV) Complexes Derived from Monoesters and ‐carboxylates of 2,5‐Dipicolinic Acid

“…Products were dried at room temperature under vacuum and stored under N 2 . The following compounds were prepared according to published procedures: 6-(methoxycarbonyl)-pyridine-3-carboxylic acid (1), [9] methyl 5-(chlorocarbonyl)pyridine-2-carboxylate, [10] myo-inositol-orthoformate, [11,12] 1,2:3,4-di-O-isopropylidene-α--galactose, [13] [VO(pic) 2 ], [14] K[VO 2 (pic) 2 ], [14] K[VO 2 (2,5dipic)]. [15] Analyses and Methods: Elemental analyses were carried out in the Analytical Laboratory of the Chemistry Department, University of Hamburg.…”

Reciprocal Donor–Acceptor Selectivity: the Influence of the Donor O‐2 Substituent in the Regioselective Mannosylation of myo‐Inositol Orthopentanoate

“…The foregoing brings to mind the interesting chemistry of Kishi's inositol orthoformate (10), [9,10] which presents two enantiotopic axial -OH groups involved in strong intramolecular H-bonds, while the equatorial -OH group is weakly H-bonded to the orthoester oxygen atoms. [11] Several studies on compound 10 have shown dramatic contrasts in regioselectivities (Table 1).…”