Structure of (±)-1,2;4,5-di-O-cyclohexylidene myo-inositol and synthesis of myo-inositol 3-phosphate via its phosphorylation with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one

Regioselective Protection and Deprotection of Inositol Hydroxyl Groups

“…In the structurally similar dicyclohexylidene diol 28 , the inositol ring adopts a distorted chair conformation. The conformation of the inositol ring is qualitatively consistent with that observed in solution by NMR spectroscopy, which suggests that the observed relative reactivity of the two hydroxyl groups in 28 cannot be attributed to the differences in their acidity or steric effects …”

Stereochemistry at Phosphorus of the Reaction Catalyzed by myo-Inositol Monophosphatase

“…The chiral phosphorylating agent (2R,4S, 5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one has been used by our group to prepare D-(+)-myo-inositol 3-phosphate. 20 The thio analogue (1) has been utilized to introduce 17 O and 18 O labels into organic thiophosphate analogues for stereochemical studies at phosphorus, [21][22][23] and here, 1 has been used to prepare D-1-S p -myo-inositol [ 17 25 A small amount of phosphorylation at the 4/6-position was also observed. Diastereomers 3 and 4 coeluted by flash chromatography but could be separated by preparative high-performance liquid chromatography (HPLC), to give pure samples of the first (δ P 82.4 ppm) and second (δ P 81.0 ppm) eluted diastereomers, which were fully characterized by 31 P, 1 H, and 13 C nuclear magnetic resonance (NMR) spectroscopy.…”

“…The chiral phosphorylating agent (2R,4S, 5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one has been used by our group to prepare D-(+)myo-inositol 3-phosphate. 20 The thio analogue (1) has been utilized to introduce 17 O and 18 O labels into organic thiophosphate analogues for stereochemical studies at phosphorus, [21][22][23] and here, 1 has been used to prepare D-1-S p -myo-inositol [ 17 O]-thiophosphate (6) (Scheme 2).…”