Pinitol diacetonide

Base Information

• Chemical Name: Pinitol diacetonide
• CAS No.: 57819-56-4
• Molecular Formula: C13H22O6
• Molecular Weight: 274.314
• ChEMBL ID: CHEMBL493528
• DSSTox Substance ID: DTXSID80584191
• Wikidata: Q82475822
• Mol file: 57819-56-4.mol

Synonyms:57819-56-4;PINITOL DIACETONIDE;D-chiro-Inositol, 3-O-methyl-1,2:5,6-bis-O-(1-methylethylidene)-;(1R,2R,6R,7S,8S,9R)-8-methoxy-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-ol;CHEMBL493528;SCHEMBL12858494;DTXSID80584191;IPNUFAHKROGNMZ-HGQQYVGVSA-N;1,2:5,6-Bis-O-(1-methylethylidene)-3-methyl-1D-chiro-inositol;AKOS015916311;(3aR,4S,5S,5aR,8aR,8bR)-5-methoxy-2,2,7,7-tetramethylhexahydrobenzo[1,2-d:3,4-d']bis([1,3]dioxole)-4-ol;AS-76674;D93531;1 2:5 6-BIS-O-(1-METHYLETHYLIDENE)-3-;W-203177;1,2:5,6-Di-O-isopropylidene-D-chiro-inositol, 98%;1,2:5,6-Di-O-isopropylidene-D-chiro-inositol, AldrichCPR;1-D-1,2:5,6-Di-O-isopropylidene-3-O-methyl-chiro- inositol;(1R,2R,6R,7S,8S,9R)-8-methoxy-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.0?,?]dodecan-7-ol;(3aR,4S,5S,5aR,8aR,8bR)-5-Methoxy-2,2,7,7-tetramethylhexahydro-2H,7H-benzo[1,2-d:3,4-d']bis[1,3]dioxol-4-ol

Chemical Property of Pinitol diacetonide

Chemical Property:

• Melting Point: 105-108 °C(lit.)
• PSA: 66.38000
• LogP: 0.41610
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 274.14163842
• Heavy Atom Count: 19
• Complexity: 368

Purity/Quality:

99% ^*data from raw suppliers

Dicyclohexylidene pinitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(C3C(C2O1)OC(O3)(C)C)OC)O)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H]([C@@H]([C@@H]3[C@H]([C@@H]2O1)OC(O3)(C)C)OC)O)C

Technology Process of Pinitol diacetonide

There total 9 articles about Pinitol diacetonide 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: 90.0%

2-Methoxypropene (116-11-0) + pinitol (10284-63-6) → 3-O-methyl-1,2:5,6-bis-O-(1-methylethylidene)-D-chiro-inositol (57819-56-4)

Guidance literature:

In N,N-dimethyl-formamide; at 80 - 82 ℃;

Reference yield: 89.0%

pinitol (10284-63-6) + 2,2-dimethoxy-propane (77-76-9) → 3-O-methyl-1,2:5,6-bis-O-(1-methylethylidene)-D-chiro-inositol (57819-56-4)

Guidance literature:

With magnesium sulfate; toluene-4-sulfonic acid; In acetone; at 20 ℃; for 16h;

DOI:10.1016/j.carres.2007.01.004

Reference yield:

pinitol (10284-63-6) + 2,2-dimethoxy-propane (77-76-9) → 1,2:4,5-di-O-isopropylidene-3-O-methyl-D-chiro-inositol (58706-05-1,96744-20-6,127062-83-3) + 3-O-methyl-1,2:5,6-bis-O-(1-methylethylidene)-D-chiro-inositol (57819-56-4)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 16h; Yield given. Yields of byproduct given;

upstream raw materials:

1L-1,2:5,6-di-O-isopropylidene-chiro-inositol

methyl iodide

pinitol

2-Methoxypropene

Refernces

• 1、 Larner, Joseph,Price, John D.,Heimark, Douglas,Smith, Leigh,Rule, Gordon,Piccariello, Thomas,Fonteles, Manasses C.,Pontes, Carla,Vale, Daniele,Huang, Laura. "Isolation, structure, synthesis, and bioactivity of a novel putative insulin mediator. A galactosamine chiro-inositol pseudo-disaccharide Mn2+ chelate with insulin-like activity". . p. 3283 - 3291. Retrieved 2003.
• 2、 -. "D-pinitol pro-drug and the method for preparing the same". Paragraph 0227; 0228; 0229. . Retrieved 2016/10/09.
• 3、 Zhan, Tianrong,Lou, Hongxiang. "Synthesis of azole nucleoside analogues of d-pinitol as potential antitumor agents". . p. 865 - 869. Retrieved 2008/02/02.