1D-5-O-methyl-chiro-inositol

Base Information

• Chemical Name: 1D-5-O-methyl-chiro-inositol
• CAS No.: 523-92-2
• Molecular Formula: C7H14O6
• Molecular Weight: 194.185
• Hs Code.: 2909499000
• DSSTox Substance ID: DTXSID301035423
• Nikkaji Number: J2.373.012J
• Wikidata: Q27102872,Q104987777
• Metabolomics Workbench ID: 51179
• Mol file: 523-92-2.mol

Synonyms:2-O-methyl-chiro-inositol;2-O-methylchiroinositol;quebrachitol;quebrachitol, (L-chiro)-isomer

Chemical Property of 1D-5-O-methyl-chiro-inositol

Chemical Property:

• Vapor Pressure: 3.28E-05mmHg at 25°C
• Refractive Index: 1.588
• Boiling Point: 317.2°C at 760mmHg
• Flash Point: 145.6°C
• PSA: 110.38000
• Density: 1.56g/cm³
• LogP: -3.18050
• Storage Temp.: Refrigerator
• Solubility.: Water
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 194.07903816
• Heavy Atom Count: 13
• Complexity: 158

Purity/Quality:

99% ^*data from raw suppliers

5-O-Methyl-myo-inositol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(C1O)O)O)O)O
• Isomeric SMILES: COC1[C@H]([C@@H](C([C@H]([C@@H]1O)O)O)O)O
• Uses: 5-O-Methyl-myo-inositol or Sequoyitol is used in the treatment of diabetes, decreasing blood glucose, improving glucose intolerance and improving insulin signalling.

Technology Process of 1D-5-O-methyl-chiro-inositol

There total 58 articles about 1D-5-O-methyl-chiro-inositol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

6,8,9-tris-benzyloxy-7-methoxy-3-phenyl-2,4-dioxa-bicyclo[3.3.1]nonane (940000-69-1) → sequoyitol (523-92-2)

Guidance literature:

palladium dihydroxide; In methanol; for 20h; Heating;

DOI:10.1016/j.tet.2007.02.096

Reference yield:

L-(+)-1,3-di-O-benzyl-6-O-acetyl-myo-inositol + methyl iodide (74-88-4) → sequoyitol (523-92-2) + D-6-O-methyl-myo-inositol (166734-75-4)

Guidance literature:

L-(+)-1,3-di-O-benzyl-6-O-acetyl-myo-inositol; methyl iodide; With silver(l) oxide; In dichloromethane; at 20 - 40 ℃; for 14h; Inert atmosphere;

With water; lithium hydroxide; In tetrahydrofuran; at 50 ℃; for 2h; Inert atmosphere;

With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; for 20h; under 2327.23 Torr; Overall yield = 0.01 g;

DOI:10.1002/ejoc.201701417

Reference yield:

(1R,2S,3R,4R,5R,6R)-2,3,5-Tris-benzyloxy-6-methoxy-cyclohexane-1,4-diol → sequoyitol (523-92-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 24h;

DOI:10.1016/0008-6215(92)85046-3

upstream raw materials:

quebrachitol

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

(4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one

1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol

Downstream raw materials:

2,3,4,5,6-Penta-O-acetyl-1-O-methyl-myo-inositol

1,2,3,4,6-penta-O-acetyl-5-O-methyl-myo-inositol

5-O-Methyl-myo-inosose-⁽²⁾; 4-O-Methyl-scyllo-inosose

inositol peracetate

Refernces

• 1、 Murali, Chebrolu,Shashidhar, Mysore S.,Gopinath, Chinnakonda S.. "Hydroxyl group deprotection reactions with Pd(OH)2/C: a convenient alternative to hydrogenolysis of benzyl ethers and acid hydrolysis of ketals". . p. 4149 - 4155. Retrieved 2007/10/03.
• 2、 Jung, Pierre M. J.,Motherwell, William B.,Williams, Alvin S.. "Stereochemical observations on the bromate induced monobromopentahydroxylation of benzene by catalytic photoinduced charge transfer osmylation. A concise synthesis of (±)-pinitol". . p. 1283 - 1284. Retrieved 2007/10/03.