67772-77-4

Basic information

• Product Name: EPIEPOFORMIN
• Synonyms: EPIEPOFORMIN
• CAS NO: 67772-77-4
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.14
• Mol File: 67772-77-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 329.2 °C at 760 mmHg
• Flash Point: 145.9 °C
• Appearance: /
• Density: 1.387 g/cm³
• Vapor Pressure: 1.34E-05mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: EPIEPOFORMIN(CAS DataBase Reference)
• NIST Chemistry Reference: EPIEPOFORMIN(67772-77-4)
• EPA Substance Registry System: EPIEPOFORMIN(67772-77-4)

Safety Data

• Hazardous Substances Data: 67772-77-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H8O3/c1-3-2-4(8)6-7(10-6)5(3)9/h2,4,6-8H,1H3/t4-,6+,7-/m0/s1

Upstream product

• 162809-82-7 (+)-(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-methyl-1-cyclohex-5-en-1-one 
• 851129-88-9 (1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol 
• 851129-90-3 (1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol 
• 119478-74-9 (S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enone 
• 96893-99-1 (1R,2S)-5,5-(Ethylendioxy)-2-hydroxycyclohexancarbonsaeure-ethylester 
• 455330-50-4 (1S)-4,4-ethylenedioxy-2-cyclohexen-1-ol 
• 532989-56-3 Acetic acid (S)-(1,4-dioxa-spiro[4.5]dec-6-en-8-yl) ester 
• 455330-49-1 (1S)-4,4-ethylenedioxy-2-iodo-1-cyclohexyl acetate 
• 455330-48-0 (1R,2S)-2-acetoxy-5,5-ethylenedioxycyclohexane carboxylic acid 
• 532989-49-4 (2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxycyclohexan-1-one 
• 532989-47-2 (1S)-1-tert-butyldimethylsilyloxy-4,4-ethylenedioxy-2-cyclohexene 
• 532989-50-7 (1R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-trimethylsilanyloxy-7-oxa-bicyclo[4.1.0]hept-2-ene 
• 532989-51-8 (2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-phenylselenylcyclohexan-1-one 
• 532989-52-9 (1R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-3-phenylselanyl-7-oxa-bicyclo[4.1.0]heptan-2-one 

Downstream Products

• 1204745-26-5 (+)-gabosine A 
• 1043454-68-7 (2R,4S,5R)-4,5-dihydroxy-2-methylcyclohexan-1-one 
• 15254-70-3 (1R,6S)-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione 

Relevant articles and documents

Synthesis of (+)-epiepoformin using the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone

Asymmetric total synthesis of (+)-epiepoformin was achieved in short steps using the base-catalyzed asymmetric Diels-Alder (DA) reaction of 3-hydroxy-2-pyrone with chiral acrylate. Since the synthesis produced Ogasawara's intermediate, it is also presented as a formal synthesis of (-)-theobroxide.

Divergent approach to gabosines and anhydrogabosines: Enantioselective syntheses of (+)-epiepoformin, (+)-EpoKformin, (+)-gabosine A, and gabosines B and F

A divergent approach to polyoxygenated methylcyclohexanes has been applied to synthesize several gabosines and anhydrogabosines. The starting hydroxycyclohexenone, which is readily available in any antipodal form, provides access to both enantiomers of the target compounds. The syntheses of anhydrogabosines involve three main transformations: α-methylation, epoxidation, and sulfur removal, whereas the syntheses of gabosines require an additional epoxide hydrolysis step. The strategy has been applied to the synthesis of (+)-epiepoformin, (+)-epoformin, (+)-gabosine A, and gabosines B and F, through straightforward sequences in good overall yields. A cyclohexenone that is easily available in any antipodal form has been used as the starting material to synthesize various gabosines and anhydrogabosines through a divergent strategy. The syntheses of anhydrogabosines involve three main transformations: α-methylation, epoxidation, and sulfur removal, whereas the syntheses of gabosines require an additional epoxide hydrolysis step. Copyright

Enantioselective synthesis of natural polyoxygenated cyclohexanes and cyclohexenes from [(p-tolylsulfinyl)methyl]-p-quinols

Exploitation of the β-hydroxysulfoxide fragment present in a number of enantiomerically pure (SR)and (SS)-[(p-tolylsulfinyl)methyl]-pquinols allowed chemo- and stereocontrolled conjugate additions of different organoaluminium reagents to the cyclohexadien

Total synthesis of (+)-epiepoformin, (+)-epiepoxydon and (+)-bromoxone employing a useful chiral building block, ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanecarboxylate

Enantioselective total synthesis of (+)-epiepoformin 1, (+)-epiepoxydon 2 and (+)-bromoxone 3 using a chiral building block, ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclo- hexanecarboxylate 6, is described. Since the synthesis afforded intermediates 18, 2 and 25, it accomplished a formal synthesis of (-)-theobroxide 19, (-)-phyllostine 22, (+)-herveynone 27 and (-)-asperpentyn 28. The usefulness of 6 for the synthesis of natural epoxycyclohexene derivatives was demonstrated.