D-Epoxone

Base Information

• Chemical Name: D-Epoxone
• CAS No.: 18422-53-2
• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.271
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID70428499
• Nikkaji Number: J773.906K
• Wikidata: Q69757995
• Mol file: 18422-53-2.mol

Synonyms:D-Epoxone;18422-53-2;Shi Epoxidation Diketal Catalyst;(3'aR,4S,7'aR)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran]-7'-one;1,2:4,5-Di-O-isopropylidene-beta-D-erythro-2,3-hexodiulo-2,6-pyranose;273202-74-7;SCHEMBL1704440;DTXSID70428499;IVWWFWFVSWOTLP-RWYTXXIDSA-N;(3a'R,4R,7a'R)-2,2,2',2'-tetramethyldihydrospiro[[1,3]dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'(4'H)-one;EX-A5739;AKOS024318948;CS-W016736;Shi Epoxidation Diketal Catalyst, 98%;AC-22437;Shi Epoxidation Diketal Catalyst, 95% purity;1,2;4,5-di-O-isopropylidene-beta-D-erythro-2,3-hexodiulo-2,6-pyranose;1-O,2-O:4-O,5-O-Diisopropylidene-3-deoxy-3-oxo-beta-D-fructopyranose

Chemical Property of D-Epoxone

Chemical Property:

• Vapor Pressure: 7.81E-05mmHg at 25°C
• Melting Point: 102-104 °C(lit.)
• Refractive Index: 1.511
• Boiling Point: 341.9 °C at 760 mmHg
• Flash Point: 150 °C
• PSA: 63.22000
• Density: 1.28 g/cm³
• LogP: 0.58500
• Storage Temp.: 2-8°C
• Solubility.: Soluble in chloroform and methanol.
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 258.11033829
• Heavy Atom Count: 18
• Complexity: 390

Purity/Quality:

98%, ^*data from raw suppliers

Shi Epoxidation Diketal Catalyst ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC2(O1)C(=O)C3C(CO2)OC(O3)(C)C)C
• Isomeric SMILES: CC1(OC[C@]2(O1)C(=O)[C@H]3[C@@H](CO2)OC(O3)(C)C)C
• Uses: 1,2:4,5-Di-O-isopropylidene-β-D-erythro-2,3-hexodiulo-2,6-pyranose is a chemical reagent used in the synthesis of Irciniastatin (A & B), cytotoxic secondary metabolites. Used in epoxidation reactions. Shi Epoxidation Diketal Catalyst is a chemical reagent used in the synthesis of Irciniastatin (A & B), cytotoxic secondary metabolites. Used in epoxidation reactions. Highly selective and active organocatalyst for the asymmetric epoxidation of alkenes with hydrogen peroxide. Green epoxidation catalyst of choice according to Glaxo-Smith-Kline''s reagent guide.An Efficient Catalytic Asymmetric Epoxidation MethodUse of an Iridium-Catalyzed Redox-Neutral Alcohol-Amine Coupling on Kilogram Scale for the Synthesis of a GlyT1 Inhibitor

Technology Process of D-Epoxone

There total 9 articles about D-Epoxone 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: 100.0%

1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose (25018-67-1) → Shi's ketone (69351-19-5,18422-53-2)

Guidance literature:

With sodium hypochlorite; tetrabutylammomium bromide; potassium bromide; 1-methyl-2-azaadamantane-N-oxyl; In dichloromethane; at 0 ℃; for 0.333333h; Product distribution / selectivity;

Reference yield: 100.0%

→ Shi's ketone (69351-19-5,18422-53-2)

Guidance literature:

With trichloroisocyanuric acid; 4-oxa-5-azahomoadamantane; sodium hydrogencarbonate; In dichloromethane; at 0 ℃; for 1.5h;

Reference yield: 95.0%

C12H20O6 (15080-25-8,18422-54-3,18604-28-9,20880-93-7,25018-67-1,83602-34-0) → Shi's ketone (69351-19-5,18422-53-2)

Guidance literature:

With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl; In acetonitrile; at 20 - 50 ℃; for 3h; Sealed tube;

DOI:10.1021/acs.joc.5b01950

upstream raw materials:

1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose

D-Fructose

2,2-dimethoxy-propane

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

Downstream raw materials:

1,2:4,5-di-O-isopropylidene-3-C-phenyl-β-D-fructopyranose

1,2;4,5-di-O-isopropylidene-β-D-fructopyranose

(5S,8R,9R)-2,2-dimethyl-10-oxo-1,3,6-trioxaspiro[4,5]decane-8,9-diyl diacetate

3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose

Refernces

• 1、 Binkley. "". . p. 1216,1219. Retrieved 1977.
• 2、 Roldan, Francisco,Gonzalez, Alberto,Palomo, Claudio. "NICOTINIUM DICHROMATE: A NEW CHEAP REAGENT FOR HIGH-YIELDING LARGE-SCALE OXIDATION OF CARBOHYDRATES". . p. C1 - C4. Retrieved 1986.
• 3、 Guo, Jiantao,Frost. "Biosynthesis of 1-deoxy-l-imino-D-erythrose 4-phosphate: A defining metabolite in the aminoshikimate pathway". . p. 528 - 529. Retrieved 2002.
• 4、 Hollenberg et al.. "". . p. 491. Retrieved 1978.
• 5、 -. "IMPROVED SYNTHESIS OF AN EPOXIDATION-CATALYST". Page/Page column 7; 8. . Retrieved 2020/07/14.
• 6、 -. "Synthesis method of fructose-derived chiral ketone catalyst". Paragraph 0012; 0013; 0014; 0031; 0032; 0033. . Retrieved 2016/10/10.