20421-13-0

Basic information

• Product Name: Crotepoxide
• Synonyms: Crotepoxide;futoxide;[1S,(+)]-3β,4β:5β,6β-Bisepoxy-6-(benzoyloxymethyl)cyclohexane-1β,2α-diol diacetate;2,3:4,5-Dianhydro-2-C-[(benzoyloxy)methyl]-D-epi-inositol 1,6-diacetate
• CAS NO: 20421-13-0
• Molecular Formula: C₁₈H₁₈O₈
• Molecular Weight: 362.332
• Mol File: 20421-13-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 467.9°Cat760mmHg
• Flash Point: 206.2°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 6.24E-09mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: Crotepoxide(CAS DataBase Reference)
• NIST Chemistry Reference: Crotepoxide(20421-13-0)
• EPA Substance Registry System: Crotepoxide(20421-13-0)

Safety Data

• Hazardous Substances Data: 20421-13-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H18O8/c1-9(19)23-13-12-14(25-12)16-18(26-16,15(13)24-10(2)20)8-22-17(21)11-6-4-3-5-7-11/h3-7,12-16H,8H2,1-2H3/t12-,13-,14-,15+,16-,18+/m1/s1

Upstream product

• 74766-77-1 DL-di-O-acetyl-(1,3/2,4,6)-3,4-dibromo-6-benzoyloxymethyl-1,2-cyclohexanediol 
• 69982-70-3 3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-5a-carba-β-DL-glucopyranosyl bromide 
• 74766-83-9 DL-1,2-di-O-acetyl-(1,4/2,3)-3,4-dibromo-6-bromomethyl-5-cyclohexene-1,2-diol 
• 74766-84-0 DL-1,2-di-O-acetyl-(1,6/2,5)-3-benzoyloxymethyl-5,6-dibromo-3-cyclohexene-1,2-diol 
• 74766-79-3 DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol 
• 74766-78-2 3,4-di-O-acetyl-1,5-anhydro-6-bromo-2,6-dideoxy-5a-carba-DL-arabino-hex-1-enitol 
• 532-32-1 sodium benzoate 
• 74766-86-2 DL-3,4-di-O-Acetyl-1,2-anhydro-(1,2,3/4)-5-benzoyloxymethyl-5-cyclohexene-1,2,3,4-tetrol 
• 17550-38-8 DL-3,4-di-O-acetyl-1,2-anhydro-(1,2/3,4)-2C-(benzoyloxymethyl)-5-cyclohexene-1,2,3,4-tetrol 
• 74766-85-1 trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]-cyclohexa-4,6-diene 
• 57987-33-4 Benzoic acid 2-acetoxy-5-hydroxy-7-oxa-bicyclo[4.1.0]hept-3-en-1-ylmethyl ester 
• 57987-34-5 Benzoic acid 2-acetoxy-5-(tetrahydro-pyran-2-yloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-1-ylmethyl ester 
• 57987-31-2 Benzoic acid (1S,2S)-2-methanesulfonyloxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-1-ylmethyl ester 
• 57987-32-3 Benzoic acid (1S,2S)-5-hydroxy-2-methanesulfonyloxy-7-oxa-bicyclo[4.1.0]hept-3-en-1-ylmethyl ester 

Relevant articles and documents

Enantiospecific syntheses of (+)-crotepoxide, (+)-boesenoxide, (+)-β- senepoxide, (+)-pipoxide acetate, (-)-iso-crotepoxide, (-)-senepoxide, and (- )-tingtanoxide from (-)-quinic acid

A convenient strategy that is ideally suited for the Construction of all the naturally occurring cyclohexane diepoxides and cyclohexene epoxides is described. The key intermediate 12, a 1,3-cyclohexadiene, has been prepared from (-)-quinic acid in 11 steps with 18% overall yield: Singlet oxygen photooxygenation of the 1,3-cyclohexadiene followed by rearrangement of the resultant endoperoxides with either cobalt-meso-tetraphenylporphyrin or trimethyl phosphite afforded enantiopure (+)-crotepoxide, (+)-boesenoxide, and (-)-iso-crotepoxide or (-)-senepoxide, (+)-β-senepoxide, (+)-pipoxide acetate, and (-)-tingtanoxide, respectively.

Conversion of β-Senepoxide to Crotepoxide: Total Synthesis of (+)-Crotepoxide

Total synthesis of (+)-crotepoxide has been accomplished by chemical conversion of (+)-β-senepoxide which was prepared from (-)-7-endo-oxabicyclohept-5-ene-2-carboxylic acid.

SYNTHESIS AND EPOXIDATION OF TRANS-5,6-DIACETOXY-1-BENZOYLOXYMETHYL-1,3-CYCLOHEXADIENE

Epoxidation of a newly prepared trans-5,6-diacetoxy-1-benzoyloxymethyl-1,3-cyclohexadiene by m-chloroperbenzoic acid in dichloroethane gave several isomeric compounds of the biologically important highly oxygenated cyclohexane derivatives.