127401-30-3

Upstream product

• 701272-07-3 3,4-di-O-allyl-1,2:5,6-di-O-isopropylidene-D-chiro-inositol 
• 700863-94-1 3,4-di-O-allyl-D-chiro-inositol 
• 40617-60-5 1,2:5,6-bis-O-(1-methylethylidene)-D-chiro-inositol 
• 110550-25-9 3,4-di-O-allyl-2,5-di-O-benzyl-D-chiro-inositol 
• 100-39-0 benzyl bromide 
• 700863-99-6 3,4-di-O-allyl-1,6-di-O-benzoyl-2,5-di-O-benzyl-D-chiro-inositol 
• 438034-46-9 (3aR,4S,7S,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-bis(phenylmethoxy)-1,3-benzodioxole 
• 219316-93-5 (3aR,4S,7S,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol diacetate 
• 158850-48-7 (3aR,4S,7S,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol 
• 438034-76-5 (1R,2S,3S,6S)-3,6-bis(phenylmethoxy)-4-cyclohexene-1,2-diol dibenzoate 
• 438034-47-0 (3aR,4R,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-bis(phenylmethoxy)-1,3-benzodioxole 
• 671193-05-8 (1S,2R,3R,6R)-3,6-Bis-benzyloxy-cyclohex-4-ene-1,2-diol 
• 438034-27-6 (3aS,4R,7R,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol 4-monoacetate 
• 219130-51-5 (3aR,4R,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol 

Relevant academic research and scientific papers

A comparative study of the influence of protecting groups on the reactivity of chiro-inositol glycosyl acceptors

The influence of protecting groups on the reactivity of glycosyl acceptors has been investigated through a series of competitive glycosylation experiments using differently substituted C2 symmetric D-chiro-inositol derivatives. It has been shown that, for

Conformation inversion of an inositol derivative by use of silyl ethers: A modified route to 3,6-di-O-substituted-L-ido-tetrahydroxyazepane derivatives

The tans-diequatorial 3,4-diol of 2,5-di-O-benzyl-D-chiro-inositol cleaved selectively with the periodate ion in the presence of the trans-diaxial 1,6-diol to give a dialdehyde (dialdose) from which 3,6-di-O-benzyl-D- mannotetrahydroxyazepane (1) was made. The trans-diaxial 1,6-diol of 3,4-di-O-allyl-2,5-di-O-benzyl-D-chiro-inositol was not cleaved satisfactorily by periodate, but replacement of the allyl substituents with tert-butyldimethylsilyl groups caused conformational inversion of the inositol ring, and the resulting trans-diequatorial 1,6-diol cleaved efficiently to give a dialdehyde from which 3,6-di-O-benzyl-L-tdo-tetrahydroxyazepane (2) can be prepared.

Facile syntheses of all possible diastereomers of conduritol and various derivatives of inositol stereoisomers in high enantiopurity from myo-inositol

Phosphoinositide-based signaling processes are crucially important in intracellular signal transduction events. Inositol phosphate analogues have been useful in probing the structure-activity relationships between inositol phosphates and biomacromolecules, and in studying biological functions of newly found inositol phosphates. Thus, a systematic and ready access to inositol stereoisomers is highly desirable. And practical and convenient syntheses of conduritols and related compounds are also important because of their biological activities and their synthetic utilities in the preparation of other bioactive molecules. We herein report the first syntheses of all possible diastereomers of conduritol and various derivatives of eight inositol stereoisomers in high enantiopurity from myo-inositol, which involve efficient enzymatic resolution of the intermediates conduritol B and C derivatives, followed by oxidation-reduction or the Mitsunobu reaction, and cis-dihydroxylation in stereo- and regioselective manners.

Membrane-permeant esters of inositol polyphosphates, chemical syntheses and biological applications

Membrane-permeant derivatives of inositol polyphosphates are useful tools for biological studies. Racemic 2,3,6-tri-O-butyryl-myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester(Bt3IP3/AM), myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester (IP3/AM), hexakis(propionyloxymethyl) ester (IP3/PM) and hexakis(butyryloxymethyl) ester (IP3/BM) were therefore synthesized. Whereas extracellular application of up to 200 μM of Bt3IP3/AM or IP3/AM to 1321N1 astrocytoma cells failed to mobilize internal calcium, IP3/PM and IP3/BM released internal calcium at concentrations as low os 20 μM and 2 μM, respectively.