92620-04-7

Basic information

• Product Name: 5-Cyclohexene-1,2,3,4-tetrol, 2-[(benzoyloxy)methyl]-, 4-benzoate, (1S,2S,3S,4R)-
• CAS NO: 92620-04-7
• Molecular Formula: C21H20O7
• Molecular Weight: 384.386
• Mol File: 92620-04-7.mol

Chemical Properties

• CAS DataBase Reference: 5-Cyclohexene-1,2,3,4-tetrol, 2-[(benzoyloxy)methyl]-, 4-benzoate, (1S,2S,3S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Cyclohexene-1,2,3,4-tetrol, 2-[(benzoyloxy)methyl]-, 4-benzoate, (1S,2S,3S,4R)-(92620-04-7)
• EPA Substance Registry System: 5-Cyclohexene-1,2,3,4-tetrol, 2-[(benzoyloxy)methyl]-, 4-benzoate, (1S,2S,3S,4R)-(92620-04-7)

Safety Data

• Hazardous Substances Data: 92620-04-7(Hazardous Substances Data)

Upstream product

• 172877-75-7 (3aS,7aR)-methyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate 
• 172877-74-6 (-)-(3aS,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylic acid 
• 172877-76-8 ((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methanol 
• 32359-20-9 (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid 
• 1379659-90-1 C₃₀H₃₈O₇Si 
• 1379659-88-7 C₁₆H₃₀O₅Si 
• 1379659-87-6 C₁₆H₂₈O₅Si 
• 1379659-86-5 tert-butyl(((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methoxy)dimethylsilane 

Downstream Products

• 78804-18-9 (+)-(1R,2S,3R,4S)-2-benzoyloxymethylcyclohex-5-ene-1,2,3,4-tetrol 1,3-diacetate 4-benzoate 
• 113467-89-3 (+)-(1R,2S,3R,4S)-2-benzoyloxymethylcyclohex-5-ene-1,2,3,4-tetrol 1,2,3-triacetate 4-benzoate 
• 113467-91-7 (+)-(1R,2R,3S,4R,5S,6R)-3-benzoyloxymethyl-7-oxabicyclo<4.1.0>heptane-2,3,4,5-tetrol 5-benzoate 
• 113467-90-6 (-)-(1R,2S,3R,4S)-2-benzoyloxymethyl-1,2-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetrol 4-benzoate 

Relevant articles and documents

Photooxygenation of a microbial arene oxidation product and regioselective Kornblum-DeLamare rearrangement: Total synthesis of zeylenols and zeylenones

We report the enantioselective total syntheses of zeylenol (+)-1, as well as its congeners (-)-7 and 16, and of 3-O-debenzoylzeylenone 28. To this end, a new variant of the Kornblum-DeLaMare rearrangement, which utilises neighbouring-group participation to impart regioselectivity, has been developed. The approach employs photooxygenation of building blocks derived from a microbial arene oxidation product. New light on a Korny rearrangement: Biooxidation of benzoic acid with R. eutrophus B9 gives a dearomatised diene diol acid that allows concise access to the zeylenol and zeylenone family of polyoxygenated cyclohexene natural products. The synthesis employs diene photooxygenation and a new regioselective variant of the Kornblum-DeLaMare endoperoxide fragmentation has been developed (see scheme).

CYCLOHEXANE OXIDE DERIVATIVES FROM KAEMPFERIA ANGUSTIFOLIA AND KAEMPFERIA SPECIES

(-)-(3S,4R,5S,7S)-5-Benzoyloxymethyl-6-oxadicyclo-hept-1-ene-3,4-diol 3-benzoate and the two (+)-zeylenol related substances, (-)-(1R,2S,3R,4S)-2-benzoyloxymethylcyclohex-5-ene-1,2,3,4-tetrol 1,4-dibenzoate, and (1R,2S,3R,4S)-2-hydroxymethylcyclohex-5-ene-1,2,3,4-tetrol 1,4-dibenzoate, together with 2'-hydroxy-4,4',6'-trimethoxychalcone, were isolated from the rhizomes of Kaempferia angustifolia, in addition to crotepoxide, boesenboxide and (+)-zeylenol.The rhizomes of an unnamed Kaempferia species have also been found to contain the zeylenol derivatives. - Keywords: Kaempferia angustifolia; Kaempferia sp.; Zingiberaceae; (-)-pipoxide; oxygenated cyclohexane; (+)-zeylenol.