6090-97-7

Usage

Uses

Used in Pharmaceutical Industry:
1-D-4-O-METHYL-MYO-INOSITOL is used as a therapeutic agent for improving insulin sensitivity and regulating glucose metabolism in conditions such as polycystic ovary syndrome (PCOS) and diabetes.
Used in Dietary Supplements:
1-D-4-O-METHYL-MYO-INOSITOL is used as a dietary supplement for its potential health benefits, including the treatment of various metabolic disorders.
Used in Research and Development:
1-D-4-O-METHYL-MYO-INOSITOL is used in ongoing research to further explore its biological functions and potential therapeutic applications in the treatment of metabolic disorders and other health conditions.

Upstream product

• 642-38-6 quebrachitol 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 85798-11-4 (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 
• 135267-00-4 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol 
• 102997-58-0 (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene 
• 133218-74-3 4,5,6-tri-O-benzyl-1,2-anhydro-myo-inositol 
• 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 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 87-89-8 D-myo-inositol 
• 77-78-1 dimethyl sulfate 
• 80971-02-4 (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol 

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 
• 17230-39-6 penta-O-acetyl-1-O-methyl-muco-inositol 
• 87-89-8 D-myo-inositol 
• 488-54-0 D-chiro-inositol 
• 10284-63-6 pinitol 
• 1158415-00-9 (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(butanoyloxy)-5-methoxycyclohexyl butanoate 
• 42442-75-1 (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate 

Relevant academic research and scientific papers

Sulfonate protecting groups. Synthesis of O- and C-methylated inositols: D- and L-ononitol, D- and L-laminitol, mytilitol and scyllo-inositol methyl ether

Syntheses of d- and l-ononitol, d- and l-laminitol, mytilitol and scyllo-inositol methyl ether starting from myo-inositol are described. One or two of the myo-inositol 1,3,5-orthoformate hydroxyl groups were protected as tosylates. These mono or ditosylat

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.

Racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate: A versatile intermediate for the preparation of myo-inositol phosphates

The versatility of racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5- orthoformate as an intermediate for the preparation of protected myo- inositol derivatives is demonstrated. Procedures described provide simple access to several protected myo-inositol derivatives which are intermediates for the preparation of myo-inositol phosphates and racemic ononitol.

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.

Total synthesis of (+)- and (-)-ononitol

A practical, five-step synthetic sequence for conversion of myo-inositol into enantiomerically pure (+)- and (-)-ononitols in 17% and 18% overall yield, respectively, has been developed.

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.

MICROBIAL OXIDATION IN SYNTHESIS: A SIX STEP PREPARATION OF (+/-)-PINITOL FROM BENZENE

Synthesis of (+/-)-pinitol in 35percent overall yield from benzene has been achieved where the key step involved microbial oxidation of benzene to cis-1,2-dihydroxycyclohexa-3,5-diene.