22350-68-1

Basic information

• Product Name: (1R)-1-L-O-methyl-myo-inositol
• Synonyms: (1R)-1-L-O-methyl-myo-inositol
• CAS NO: 22350-68-1
• Molecular Weight: 194.185
• Mol File: 22350-68-1.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (1R)-1-L-O-methyl-myo-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-1-L-O-methyl-myo-inositol(22350-68-1)
• EPA Substance Registry System: (1R)-1-L-O-methyl-myo-inositol(22350-68-1)

Safety Data

• Hazardous Substances Data: 22350-68-1(Hazardous Substances Data)

Usage

General Description

"(1R)-1-L-O-methyl-myo-inositol" is a chemical compound that belongs to the family of inositol derivatives. It is a stereoisomer of myo-inositol, with a methyl group attached to the O-position. Inositol derivatives are known for their numerous biological functions, including acting as signaling molecules, cell membrane components, and cofactors for various enzymes. (1R)-1-L-O-methyl-myo-inositol has been studied for its potential role in modulating insulin sensitivity and glucose metabolism, making it a potential therapeutic target for conditions such as diabetes and metabolic syndrome. Additionally, it has been investigated for its potential neuroprotective and anti-inflammatory properties, suggesting a possible role in the treatment of neurological disorders and inflammatory conditions. Overall, (1R)-1-L-O-methyl-myo-inositol represents a promising compound with diverse physiological functions and potential therapeutic applications.

Upstream product

• 642-38-6 quebrachitol 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 111015-74-8 DL-1,3-di-O-benzoyl-4-O-methyl-chiro-inositol 
• 111392-26-8 (3aS,4S,4aR,7aR,8S,8aR)-4-Methoxy-8-(4-methoxy-benzyloxy)-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole 
• 71-43-2 benzene 
• 86504-06-5 cis-3,5-cyclohexadiene-1,2-diol dibenzoate 
• 111015-71-5 (1α,2α,5β,6Sb)-5,6-epoxy-3-cyclohexene-1,2-diol dibenzoate 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 
• 133218-74-3 4,5,6-tri-O-benzyl-1,2-anhydro-myo-inositol 
• 102997-58-0 (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene 
• 135267-00-4 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol 
• 85798-11-4 (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 

Downstream Products

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

Relevant articles and documents

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.

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.

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.