804. Cyclitols. Part IX. Cyclohexylidene derivatives of myoinositol

Abstract

O-cyclohexylidenemyoinositol. The preparation of lJ4,5,6-tetra-O-acety1myoinositol in good yield is described. 1 I 2-O-Cyclopentylidenemyoinositol has also been synthesised.IN Part I of this Series the conversion of cyclitols into their ketals with acetone was described. These compounds proved to be key intermediates for much subsequent work and,

Design and Synthesis of Aminocyclopentanol Glycosidase Inhibitors: Modification of Mannostatin A and Trehazolamine

“…Especially, cyclopentanol synthesis first described by Angyal et al [8,9], starting from myo-inositol, was demonstrated to be very effective for inaccessible cyclopentitol derivatives. Incorporation of an amino and/or thiol function into a cyclopentane ring to replace a hydroxyl group can be performed by replacement of activated hydroxyls with an azide and/or thiolate ion.…”

“…In 1970, elegant synthesis of 5-amino-1,2,3,4-cyclopentanetetrols by base-catalyzed aldol condensation of nitromethane and dialdehyde 6, derived from 1,2-O-cyclohexylidene-myo-inositol (5) [9], was reported [10], Fig. (2).…”

Synthesis and Two‐photon Photolysis of 6‐(ortho‐Nitroveratryl)‐Caged IP3 in Living Cells

“…Starting from 2,3:4,5-di-O-cyclohexylidene-inositol, [11] the ortho-nitroveratryl caging group was introduced at the 6-position by regioselective attack of the tin ketal [12] with ortho-nitroveratrylbromide,…”

Synthesis and Glycosidase Inhibitory Activity of Five Stereoisomers of 5-Amino-5-C-methyl-1,2,3,4-cyclopentanetetrol

“…oxidation of DL-1,2-O-cyclohexylidene-myo-inositol, followed by reduction and deprotection. Recently, Winkler rived by treatment of -1,2-O-cyclohexylidene-myo-inosiand his coworkers [4] have proposed adequate corretol [11] with excess of sodium metaperiodate has been carried lationship by comparing the structures of some α-mannoout for synthesis of the target compounds. Concerning conforaration of aminocyclitols and amino sugars.…”

“…Biological assay of Discovery of the potent and specific α-mannosidase in-seemed of interest to elucidate the influence of the C-methyl functions toward the inhibitory potentials, comparing the hibitor mannostatin A [1] (1) has stimulated us to develop new glycosidase inhibitors composed of 5-amino-1,2,3,4-activities of 7 and 8 with those of 2 and 3. cyclopentaneterols, which are thought to act as transition Dialdehyde/nitromethane cyclization has established itstate mimickings of glycopyranosyl cations postulated to self as a generally applicable synthetic method for prepform during hydrolysis of glycosides [2] . Recently, Winkler rived by treatment of -1,2-O-cyclohexylidene-myo-inosiand his coworkers [4] have proposed adequate corretol [11] with excess of sodium metaperiodate has been carried lationship by comparing the structures of some α-mannoout for synthesis of the target compounds. [8] Some nitromational feature of the transition state mannopyranosyl alkanes and alkanols have successfully been applied [9] [10] in cation predicted in hydrolysis of mannopyranosides, it the reaction of glutaraldehyde, producing some unaccessible seemed rather difficult to correlate the structures of the branched-chain aminocyclitols.…”