40617-60-5

Usage

Uses

Used in Pharmaceutical Industry:
1,2:5,6-BIS-O-(1-METHYLETHYLIDENE)-1Dis used as a precursor for the development of Lactate dehydrogenase A (LDH-A) inhibitors. These inhibitors are designed to target and halt the growth of cancer cells by blocking their glycolysis pathway, specifically the interconversion of lactate and pyruvate catalyzed by LDH-A. This innovative approach has the potential to provide new therapeutic options for cancer treatment.
In addition to its role in the development of antitumor agents, 1,2:5,6-BIS-O-(1-METHYLETHYLIDENE)-1Dmay also find applications in other areas of the pharmaceutical industry, such as drug delivery systems or as a component in the synthesis of other bioactive compounds. However, further research and development are necessary to fully explore and understand its potential applications and benefits.

Upstream product

• 168751-30-2 1,2:3,4:5,6-tri-O-isopropylidene-D-chiro-inositol 
• 77-76-9 2,2-dimethoxy-propane 
• 488-58-4 epi-Inositol 
• 38643-29-7 (+/-)-O¹,O²;O³,O⁴;O⁵,O⁶-triisopropylidene-epi-inositol 
• 116-11-0 2-Methoxypropene 
• 87-89-8 D-myo-inositol 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 115072-67-8 (3aR,4S,5S,5aR,8aR,8bS)-2,2,7,7-Tetramethyl-4,5-bis-[((E)-propenyl)oxy]-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxole 
• 115072-66-7 (±)-5,6-di-O-benzoyl-1,2:3,4-di-O-isopropylidene-myo-inositol 
• 115072-69-0 5,6-di-O-allyl-1,2:3,4-di-O-isopropylidene-myo-inositol 
• 115072-66-7 (±)-3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol 

Downstream Products

• 280745-35-9 2,3:4,5-Di-O-isopropylidene-D-manno-hexodialdose 
• 120679-73-4 1D-1,2:5,6-di-O-isopropylidene-3,4-di-O-benzyl-chiro-inositol 
• 769931-80-8 1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol 
• 769931-71-7 1-D-3-O-(3-phenyl-3-phenylthiopropanoyl)-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol 
• 769931-72-8 1-D-3-O-(3-phenyl-3-benzylthiopropanoyl)-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol 
• 769931-73-9 1-D-3-O-(3-phenyl-3-o-aminophenylthiopropanoyl)-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol 
• 110522-70-8 3,4-di-O-allyl-2,5-di-O-benzyl-L-ido-hexodialdose 
• 110550-25-9 3,4-di-O-allyl-2,5-di-O-benzyl-D-chiro-inositol 
• 227196-03-4 D-2,5-di-O-benzyl-chiro-inositol 
• 700863-94-1 3,4-di-O-allyl-D-chiro-inositol 
• 700863-95-2 2,5-di-O-benzyl-D-manno-hexodialdose 
• 700863-96-3 N-benzyl-3,6-di-O-benzyl-D-manno-3,4,5,6-tetrahydroxyazepane 
• 700863-98-5 N-benzyl-3,6-di-O-benzyl-L-ido-3,4,5,6-tetrahydroxyazepane 
• 700864-03-5 2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-L-ido-hexodialdose 

Relevant academic research and scientific papers

Monoesterification of di-O-isopropylidene and di-O-cyclohexylidene chiro-inositols

Monoesterification of D- or L-chiro-inositols protected as diacetals proceeds in excellent selectivity and yields. The metal-catalyzed, one-step reaction proceeds at room temperature under an air atmosphere and has been developed using a range of examples

H2SO4-silica: An eco-friendly heterogeneous catalyst for the differential protection of myo-inositol hydroxyl groups

There is enormous interest in myo-inositol derivatives as they serve as precursors for the synthesis of several biologically important phosphoinositols, natural products, catalyst, supramolecular architectures etc. However the presence of six secondary hy

Chemoselective alcoholysis/acetolysis of trans-ketals over cis-ketals and its application in the total synthesis of the cellular second messenger, d-myo-inositol-1,4,5-trisphosphate

The involvement of natural phosphoinositols in various cellular signalling processes and the use of synthetic inositol derivatives in catalysis, supramolecular chemistry, natural product synthesis etc. gave momentum to myo-inositol chemistry. The presence of six secondary hydroxyl groups necessitates efficient protection-deprotection strategies for the synthesis of inositol derivatives. An important strategy for the initial protection of myo-inositol is the di-ketalization, which gives a mixture of three diketals, each having both cis-fused and trans-fused ketals. It is important to have methodologies either to selectively hydrolyze one of the two ketals or to convert one of the two acid labile ketals to an orthogonal base labile protecting group. By exploiting the difference in strain between trans-ketals and cis-ketals, we developed two operationally simple, high yielding methodologies for the chemoselective hydrolysis/acetolysis of trans-ketals (both isopropylidene and cyclohexylidene) of inositols, leaving the cis-ketal undisturbed, using cheap and easily preparable H2SO 4-silica as the catalyst. Also, terminal ketal moieties of carbohydrates and acyclic polyols could be selectively hydrolyzed/acetolyzed leaving the internal ketals intact. The use of methanol as the solvent leads to chemoselective alcoholysis but the use of DCM and acetic anhydride leads to chemoselective acetolysis. Applying this methodology, a short synthesis of d-myo-inositol-1,4,5-trisphosphate has been achieved. The Royal Society of Chemistry.

Method of Treating Endothelial Dysfunction, Oxidative Stress and Related Diseases

A composition, either as a nutritional supplement or pharmaceutical, for the treatment of oxidative stress, endothelial dysfunction and related disease states which comprises administration of D-chiroinositol (DCI) congeners, acting as an antioxidant or g

Synthesis of new hexosaminyl D- and L-chiro-inositols related to putative insulin mediators

We have developed an efficient synthetic strategy to HexNH 2-α(1→3)-L-chiro-inositol (XII-XIII) and HexNH 2-α(1→2)-D-chiro-inositol (XIV-XV) based on the regio and stereoselective glycosylation of tetrabenzoyl-L-chiro-inositol 2 and

(±)-1,2:5,6-Di-O-isopropylidene-myo-inositol and (±)-6-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol: A practical preparation of key intermediates for myo-inositol phosphates

A simple and practical synthetic procedure for the versatile intermediates, (±)-1,2:5,6-di-O-isopropylidene-myo-inositol and (±)-6-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol, is described.

New syntheses of 1D- and 1L-1,2-anhydro-myo-inositol and assessment of their glycosidase inhibitory activities

The 1D and 1L enantiomers of 1,2-anhydro-myo-inositol (conduritol B epoxide) were synthesised from 1d-pinitol and 1l-quebrachitol, respectively, and their activities were compared in selected glycosidase inhibition assays. The 1d enantiomer was found to be the active isomer, functioning as an irreversible inhibitor of sweet almond β-D-glucosidase. Neither isomer was active against the α-D-glucosidase from Bacillus stearothermophilus or the β-D-galactosidase from Aspergillus oryzae. (C) 2000 Elsevier Science Ltd.

Practical synthesis of all inositol stereoisomers from myo-inositol

Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.

A convenient synthesis of D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3) and L-myo-inositol 1,4,5-trisphosphate (Ins(3,5,6)P3)

An efficient synthesis of an optically active inositol derivative that is a precursor to D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3, (-)) is described. Crystallization of the diastereomers of (±) -1-O-[(+)- menthoxycarbonyl]-6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol diastereomers from methanol gives only one diastereomer. Alkaline hydrolysis gives the useful inositol derivative (-)-6-O-benzyl-2,3:4,5-di-O- isopropylidene-myo-inositol. Likewise, crystallization of the diastereomers of (±)-3-O-[(-)-menthoxycarbonyl]-4-O-benzyl-1,2:5,6-di-O-isopropylidene- myo-inositol from methanol gave a pure compound which could be hydrolyzed to give (+)-4-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol, a precursor to D-myo-inositol 3,5,6-trisphosphate (Ins(3,5,6)P3, (+)). The ease with which these enantiomerically pure inositol derivatives were isolated may facilitate the synthesis of more complex inositol phosphate derivatives such as D-myo- inositol 1,3,4,5-tetrakisphosphate.

Regioselective functionalizations and conformational studies of di-O-isopropylidene-myo-inositol derivatives

(+/-)-1,2:4,5-Di-O-isopropylidene-myo-inositol (5) and (+/-)-1,2:5,6-di-O-isopropylidene-myo-inositol (6) could be regioselectively functionalized in reactions including alkylation, acylation, and silylation at HO-3 in preference to HO-6 and HO-4, respectively, under specific conditions.The presence of intramolecular hydrogen bonding was evident in IR and 1H NMR spectra, and the HO-3 group was identified as the hydrogen-bonding donor in 5 and 6.In their crystalline states, diol 5 prefers a chair conformation and diol 6 a twist boat (skew) conformation.Both compounds appear to have substantial populations of chair conformations in the gas and solution phases, on the basis of the MM-2 energy minimizations and comparisons of vicinal coupling constants observed in the 1H NMR spectra (in CDCl3 and Me2SO-d6) and calculated from the crystal and MM-2 conformations.It is suggested as an explanation for the observed selectivities that the kinetic acidity of the HO-3 group may be enhanced through its intramolecular hydrogen bonding with the cis-vicinal oxygen, or the nucleophilicity of the 3-alkoxide may be enhanced due to its interaction with the cis-vicinal oxygen in a manner similar to the through-space α-effect.