40617-60-5

Basic information

• Product Name: 1 2:5 6-BIS-O-(1-METHYLETHYLIDENE)-1D-
• Synonyms: 1 2:5 6-BIS-O-(1-METHYLETHYLIDENE)-1D-;1,2:5,6-BIS-O-(1-METHYLETHYLIDENE)-1D-CH;D-chiro-Inositol, 1,2:5,6-bis-O-(1-methylethylidene)-;D-CHLOROINOSITOL DIACETONIDE
• CAS NO: 40617-60-5
• Molecular Formula: C₁₂H₂₀O₆
• Molecular Weight: 260.2836
• Mol File: 40617-60-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 153-156 °C(lit.)
• Boiling Point: 395°Cat760mmHg
• Flash Point: 192.7°C
• Appearance: /
• Density: 1.24g/cm³
• CAS DataBase Reference: 1 2:5 6-BIS-O-(1-METHYLETHYLIDENE)-1D-(CAS DataBase Reference)
• NIST Chemistry Reference: 1 2:5 6-BIS-O-(1-METHYLETHYLIDENE)-1D-(40617-60-5)
• EPA Substance Registry System: 1 2:5 6-BIS-O-(1-METHYLETHYLIDENE)-1D-(40617-60-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 40617-60-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,2:5,6-BIS-O-(1-METHYLETHYLIDENE)-1Dis used as a precursor for the development of Lactate dehydrogenase A (LDH-A) inhibitors. These inhibitors are designed to target and halt the growth of cancer cells by blocking their glycolysis pathway, specifically the interconversion of lactate and pyruvate catalyzed by LDH-A. This innovative approach has the potential to provide new therapeutic options for cancer treatment.
In addition to its role in the development of antitumor agents, 1,2:5,6-BIS-O-(1-METHYLETHYLIDENE)-1Dmay also find applications in other areas of the pharmaceutical industry, such as drug delivery systems or as a component in the synthesis of other bioactive compounds. However, further research and development are necessary to fully explore and understand its potential applications and benefits.

Upstream product

• 168751-30-2 1,2:3,4:5,6-tri-O-isopropylidene-D-chiro-inositol 
• 38643-29-7 (+/-)-O¹,O²;O³,O⁴;O⁵,O⁶-triisopropylidene-epi-inositol 
• 116-11-0 2-Methoxypropene 
• 87-89-8 D-myo-inositol 
• 115072-66-7 (±)-5,6-di-O-benzoyl-1,2:3,4-di-O-isopropylidene-myo-inositol 
• 115072-69-0 5,6-di-O-allyl-1,2:3,4-di-O-isopropylidene-myo-inositol 
• 115072-67-8 (3aR,4S,5S,5aR,8aR,8bS)-2,2,7,7-Tetramethyl-4,5-bis-[((E)-propenyl)oxy]-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxole 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 77-76-9 2,2-dimethoxy-propane 
• 115072-66-7 (±)-3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 488-58-4 epi-Inositol 

Downstream Products

• 280745-35-9 2,3:4,5-Di-O-isopropylidene-D-manno-hexodialdose 
• 129507-93-3 (1R,2S,3S,4S,5S,6R)-6-((2R,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2,3,4,5-pentaol 
• 129568-93-0 (1R,2S,3S,4S,5S,6R)-6-((2R,3R,4R,5R,6R)-3-Amino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2,3,4,5-pentaol 
• 39248-61-8 (+/-)-O⁶-acetyl-O¹,O²;O³,O⁴-diisopropylidene-O⁵-(toluene-4-sulfonyl)-epi-inositol 
• 122596-73-0 (+/-)-O¹,O²;O³,O⁴-diisopropylidene-O⁵,O⁶-bis-(4-nitro-benzenesulfonyl)-epi-inositol 
• 280745-36-0 (3R,4R,5R,6R)-N-Benzhydryl-3,4:5,6-bis(isopropylidenedioxy)azepane 
• 120710-66-9 (1S,2S,3S,4R,5S,6R)-5,6-di(benzyloxy)cyclohexane-1,2,3,4-tetrol 
• 110550-28-2 (+)-(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrakisbenzyloxy-7-oxabicyclo[4.1.0]heptane 
• 110550-24-8 1D-2,3,4,5-tetra-O-benzyl-chiro-inositol 
• 6090-95-5 (+)-(1R,2R,3S,4S,5R,6S)-2,3,4,5-tetraol-7-oxabicyclo[4.1.0]heptane 
• 700864-01-3 1,6-di-O-benzoyl-2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-D-chiro-inositol 
• 700863-99-6 3,4-di-O-allyl-1,6-di-O-benzoyl-2,5-di-O-benzyl-D-chiro-inositol 
• 700864-04-6 N-benzyl-3,6-di-O-benzyl-4,5-bis-O-(tert-butyldimethylsilyl)-L-ido-3,4,5,6-tetrahydoxyazepane 
• 700864-00-2 1,6-di-O-benzoyl-2,5-di-O-benzyl-D-chiro-inositol 

Relevant articles and documents

Monoesterification of di-O-isopropylidene and di-O-cyclohexylidene chiro-inositols

Monoesterification of D- or L-chiro-inositols protected as diacetals proceeds in excellent selectivity and yields. The metal-catalyzed, one-step reaction proceeds at room temperature under an air atmosphere and has been developed using a range of examples

Chemoselective alcoholysis/acetolysis of trans-ketals over cis-ketals and its application in the total synthesis of the cellular second messenger, d-myo-inositol-1,4,5-trisphosphate

The involvement of natural phosphoinositols in various cellular signalling processes and the use of synthetic inositol derivatives in catalysis, supramolecular chemistry, natural product synthesis etc. gave momentum to myo-inositol chemistry. The presence of six secondary hydroxyl groups necessitates efficient protection-deprotection strategies for the synthesis of inositol derivatives. An important strategy for the initial protection of myo-inositol is the di-ketalization, which gives a mixture of three diketals, each having both cis-fused and trans-fused ketals. It is important to have methodologies either to selectively hydrolyze one of the two ketals or to convert one of the two acid labile ketals to an orthogonal base labile protecting group. By exploiting the difference in strain between trans-ketals and cis-ketals, we developed two operationally simple, high yielding methodologies for the chemoselective hydrolysis/acetolysis of trans-ketals (both isopropylidene and cyclohexylidene) of inositols, leaving the cis-ketal undisturbed, using cheap and easily preparable H2SO 4-silica as the catalyst. Also, terminal ketal moieties of carbohydrates and acyclic polyols could be selectively hydrolyzed/acetolyzed leaving the internal ketals intact. The use of methanol as the solvent leads to chemoselective alcoholysis but the use of DCM and acetic anhydride leads to chemoselective acetolysis. Applying this methodology, a short synthesis of d-myo-inositol-1,4,5-trisphosphate has been achieved. The Royal Society of Chemistry.

Synthesis of new hexosaminyl D- and L-chiro-inositols related to putative insulin mediators

We have developed an efficient synthetic strategy to HexNH 2-α(1→3)-L-chiro-inositol (XII-XIII) and HexNH 2-α(1→2)-D-chiro-inositol (XIV-XV) based on the regio and stereoselective glycosylation of tetrabenzoyl-L-chiro-inositol 2 and