Muco-Inositol

R)j-L-3-0-Benzyl-4,5-O-isopropylidene-6-O-[2-(5,5-dimethyl-l,3-dioxan-2-yl)ethyl]-2-0-(l-phenylethyl)-muco-inositol and [S(R)]-D-4-0-Benzyl-2,3-0-isopropylidene-6-0-[2-(5,5-dimethyl-l,3-dioxan-2-yl)ethyl]-5-0-(l-phenylethyl)-myo-inositol ... 

The l,3-dioxane-2-ethanol (2 ml) was added dropwise to sodium hydride (396 mg of 60% dispersion, 10 mmol) at RT under argon. When the effervescence had ceased, l l,N,N, N -tetramethylenediamine (TMEDA) (1 ml) was added, the mixture stirred for a further 4 h and then a solution of the epoxide (396 mg, 1.0 mmol) in TMEDA (1.0 ml) was added dropwise. The mixture was stirred at 100-110°C for 3 days and then allowed to cool to RT. Water was added and, after 5 min the mixture extracted with ether. The extract was washed with water and the aqueous phase reextracted with ether. The combined organic extracts were dried (MgS04) and evaporated in vacuum column chromatography (4% MeOH-10% ether-86% petrol) of the residue afforded [2(R)]-L-3-0-Benzyl-4,5-0-isopropylidene-6-0-[2-(5,5-dimethyl-l,3-dioxan-2-yl)ethyl]-2-0-(l-phenylethyl)-muco-inositol (176 mg, 31%), [a]D20 +63.4° (c 1.4, CHCI3) and [S(R)]-D-4-0-Benzyl-2,3-0-isopropylidene-6-0-[2-(5,5-dimethyl-l,3-dioxan-2-yl)ethyl]-5-0-(phenylethyl)-myo-inositol (273 mg, 48%), mp 108°-110°C, [a]D20+ 29.3° (c 0.76, CHCI3) as a thick oil and a white solid respectively, and starting epoxide (65 mg, 16%). 

Sommer, C, B. Thonke, and M. Popp (1990). The compatibility of D-pinitol and ID-l-O-methyl-muco-inositol with malate dehydrogenase. Bot. Acta 103 270-273. 

The catalytic oxidation of inositols having three axial hydroxyl groups leads again to the formation of monoketones only. Again, the reaction is remarkably selective. Angyal oxidized muco-inositol (50) to the inosose... 

The high proportion of muco-inositol formed in the isomerization is surprising. The isomerization of mj/o-inositol with acetic acid-sulturic acid (see Section VI, p. 190) gives an equilibrium mixture of myo-, DL-chtro-, and mwco-inositol in the ratios of 54 41 5. These ratios correspond to the relative thermodynamic stabilities of the three inositols as determined on the basis of intramolecular, steric interactions of the substituents, whereas the isomerization in hydrogen fluoride gives the thermodynamically least-stable isomer (muco) in the highest yield. This discrepancy can be rationalized if it is postulated that the acetoxonium ion in the mwco-inositol system is further stabilized as a di-cation of structure 138, formed because... 

Inositols are isomerized during 12 days at 117° to an equilibrium mixture, and the reaction proceeds with high stereospecificity. Thus, myo-inositol (233) is isomerized in two steps by way of DL-chiro-inositol (234) to give muco-inositol (235), and the equilibrium pro-... 

Acyclic and Alicyclic Compounds. - Pentaerythritol, D-galactitol and D-mannitol diarsenite (both 1,2,4 3,5,6-structures), and muco-inositol. ... 

Benzyl, l,2 4,5-di-0-isopropylidene 3-O-Benzy 1-1,2 4,5-di-0-isopropylidene-muco-inositol [58706-24-4]... 

Various reactions of 2,3-anhydro-l,5,6-tri-O-mesyl-epi-inositol have been used to prepare 3-substituted-muco-inositol derivatives... 

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