22350-68-1

Usage

Uses

Used in Pharmaceutical Industry:
(1R)-1-L-O-methyl-myo-inositol is used as a potential therapeutic target for conditions such as diabetes and metabolic syndrome due to its role in modulating insulin sensitivity and glucose metabolism.
Used in Neurological Applications:
(1R)-1-L-O-methyl-myo-inositol is used as a potential treatment for neurological disorders and inflammatory conditions due to its neuroprotective and anti-inflammatory properties.

Upstream product

• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 111446-91-4 (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol 
• 80971-00-2 1D-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-3-O-methyl-myo-inositol 
• 87-89-8 D-myo-inositol 
• 77-78-1 dimethyl sulfate 
• 98906-32-2 (±)-1,4-di-O-allyl-2,3:5,6-di-O-isopropylidene-myo-inositol 
• 98906-33-3 (±)-1,4-di-O-allyl-2,3-O-isopropylidene-myo-inositol 
• 98906-34-4 (±)-2,3-O-isopropylidene-1,4-di-O-allyl-6-O-benzyl-myo-inositol 
• 98906-26-4 (3aR,4R,5S,6S,7R,7aS)-5,6-Bis-allyloxy-4,7-bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 98906-29-7 (1R,2S,3R,4R,5S,6R)-2,4,5-Tris-allyloxy-3,6-bis-benzyloxy-cyclohexanol 
• 111015-72-6 (1α,2β,3β,6β)-6-methoxy-4-cyclohexene-1,2,3-triol 2,3-dibenzoate 
• 111015-74-8 DL-1,3-di-O-benzoyl-4-O-methyl-chiro-inositol 
• 111392-30-4 1-O-allyl-4-O-methyl-myo-inositol 

Downstream Products

• 54324-59-3 2,3,4,5,6-Penta-O-acetyl-1-O-methyl-myo-inositol 
• 14199-75-8 (1R,2S,3R,4R,5S,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane 
• 23887-12-9 scyllo-inositol methyl ether 
• 94482-10-7 1L-1-O-methyl-myo-inositol pentaacetate 
• 87-89-8 D-myo-inositol 
• 160712-73-2 Phosphoric acid dibenzyl ester (1S,2S,3R,4R,5S,6R)-2-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-(1-ethoxy-ethoxy)-5-methoxy-cyclohexyl ester 
• 160712-67-4 C₃₉H₄₀O₁₀ 
• 160712-70-9 C₃₁H₃₂O₈ 
• 14199-75-8 (1R,2R,3R,4R,5S,6R)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane 

Relevant academic research and scientific papers

A synthetic cyclitol-nucleoside conjugate polyphosphate is a highly potent second messenger mimic

Reactions that form sec-sec ethers are well known, but few lead to compounds with dense functionality around the O-linkage. Replacement of the α-glucopyranosyl unit of adenophostin A, a potent d-myo-inositol 1,4,5-trisphosphate (IP3R) agonist, with a d-chiro-inositol surrogate acting substantially as a pseudosugar, leads to "d-chiro-inositol adenophostin". At its core, this cyclitol-nucleoside trisphosphate comprises an ether linkage between the axial 1-hydroxyl position of d-chiro-inositol and the 3′-hydroxyl group of an adenosine ribose sugar. A divergent synthesis of d-chiro-inositol adenophostin has been achieved. Key features of the synthetic strategy to produce a triol for phosphorylation include a new selective mono-tosylation of racemic 1,2:4,5-di-O-isopropylidene-myo-inositol using tosyl imidazole; subsequent conversion of the product into separable camphanate ester derivatives, one leading to a chiral myo-inositol triflate used as a synthetic building block and the other to l-1-O-methyl-myo-inositol [l-(+)-bornesitol] to assign the absolute configuration; the nucleophilic coupling of an alkoxide of a ribose pent-4-ene orthoester unit with a structurally rigid chiral myo-inositol triflate derivative, representing the first sec-sec ether formation between a cyclitol and ribose. Reaction of the coupled product with a silylated nucleobase completes the assembly of the core structure. Further protecting group manipulation, mixed O- and N-phosphorylation, and subsequent removal of all protecting groups in a single step achieves the final product, avoiding a separate N6 protection/deprotection strategy. d-chiro-Inositol adenophostin evoked Ca2+ release through IP3Rs at lower concentrations than adenophostin A, hitherto the most potent known agonist of IP3Rs.

Synthetic tools for studying the chemical biology of InsP8

To synthesise stabilised mimics of InsP8, the most phosphorylated inositol phosphate signalling molecule in Nature, we replaced its two diphosphate (PP) groups with either phosphonoacetate (PA) or methylenebisphosphonate (PCP) groups. Utility of the PA and PCP analogues was verified by structural and biochemical analyses of their interactions with enzymes of InsP8 metabolism.

Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis

Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.

A Definitive Synthesis of D-myo-Inositol 1,4,5,6-Tetrakisphosphate and Its Enantiomer D-myo-Inositol 3,4,5,6-Tetrakisphosphate from a Novel Butane-2,3-diacetal-Protected Inositol

New and rapid syntheses of the enantiomeric intracellular signalling molecules D-myo-inositol 1,4,5,6-tetrakisphosphate (1a) and D-myo-inositol 3,4,5,6-tetrakisphosphate (1b) are described. The synthetic strategy employs the novel butane-2,3-diacetal-prot

L-α-phosphatidyl-D-myo-inositol 3,5-bisphosphate: Total synthesis of a new inositol phospholipid via myo-inositol orthoacetate

The synthesis from myo-inositol of a newly-discovered inositol phospholipid, phosphatidylinositol 3,5-bisphosphate [PtdIns(3,5)P2], is described. The synthetic strategy, employing inter alia, a trimethylaluminium-mediated regioselective cleavage of a protected myo- inositol orthoacetate followed by an optical resolution using (R)-(-)-5-oxo- 2-tetrahydrofurancarboxylate esters, allows rapid access to dipalmitoyl PtdIns(3,5)P2.

Stereochemical observations on the bromate induced monobromopentahydroxylation of benzene by catalytic photoinduced charge transfer osmylation. A concise synthesis of (±)-pinitol

The use of lower temperatures in the title reaction favours the formation of the neo diastereoisomer of the deoxybromoinositol whose diisopropylidene derivative can be converted in three steps to (±)-pinitol.

An effective strategy for the synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-phosphate related to putative insulin mimetics

Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

Approaches to the synthesis of glycosyl phosphatidyl inositols. Enantioselective synthesis of optically active chiro- and myo-inositols

An efficient synthetic strategy to optically active conveniently substituted D-chiro (5) and D-myo-inositol (10) derivatives has been developed starting from methyl α-D-glucopyranoside. Compounds 5 and 10 constitute valuable intermediates for the preparation of glycosyl phosphatidyl inositols.

Mikrobial Oxidation in Synthesis: Preparation of (+)- and (-)-Pinitol from Benzene

Microbial oxidation with Pseudomonas putida of benzene affords cis-1,2-dihydroxycyclohexa-3,5-diene (2) which may be converted in five steps and 49percent overall yield to (+/-)-pinitol.Resolution of an intermediate alcohol (6) with menthoxyacetyl chloride provides optically pure materials which may be independently transformed to (+)- or (-)-pinitol.Demethylation conditions for pinitol together with further reactions of (2) and related compounds were investigated.

The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates

Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for 'temporary' protection.The benzyl ethers are required as intermediates for the synthesis of the 'second messenger', inositol 1,4,5-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.