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

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

• 108-24-7 acetic anhydride 
• 64011-11-6 Benzoic acid (1R,2R,4S,5S,6S,7R)-5,6-dihydroxy-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester 
• 175979-34-7 4-benzoyloxymethyl-3,8-dioxatricyclo[5.1.0.0^2,4]octane-5,6-diol 5-acetate 
• 130021-74-8 (1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol 
• 131221-89-1 (1R,2R,3S)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol 
• 98-88-4 benzoyl chloride 
• 96247-02-8 (2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene 
• 203317-81-1 (1R,2R,3S)-5-(benzoyloxymethyl)-1,2-O-cyclohexylidene-4-cyclohexene-1,2,3-triol 
• 175979-30-3 Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester 
• 175979-29-0 Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester 
• 175979-28-9 (1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 
• 203317-83-3 (1R,2R,3S,4R)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidene-5-cyclohexene-1,2,3,4-tetrol 
• 175979-32-5 Benzoic acid (1S,4S,7S,8S)-7-acetoxy-8-hydroxy-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester 
• 174966-54-2 (1R,2R,3S)-3-O-tert-butyldimethylsilyl-5-benzoyloxymethyl-1,2-O-cyclohexylidene-4-cyclohexen-1,2,3-triol 

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.

First enantiospecific syntheses of crotepoxide and iso-crotepoxide from (-)-quinic acid

The optically active crotepoxide 1 and iso-crotepoxide 2 have been constructed from quinic acid involving a singlet oxygen photooxygenation as the key step.

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.

The title substituted 1,3-cyclohexadiene was prepared in three steps from the readily available DL-1,2-di-O-acetyl-(1,3/2)-3-bromomethyl-5-cyclohexene-1,2-diol. Epoxidation of it with m-chloroperoxybenzoic acid in 1,2-dichloroethane afforded several stere

STEREOSELECTIVE SYNTHESIS OF (+/-)-SENEPOXYDE AND (+/-)-CROTEPOXIDE

Stereoselective synthesis of (+/-)-senepoxyde and (+/-)-crotepoxyde is described starting from 2-hydroxymethyl-1,4-benzoquinone through the retro-Diels-Alder reaction.

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.