Epoxyquinol C
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| Category | Others |
| Catalog number | BBF-00855 |
| CAS | |
| Molecular Weight | 388.37 |
| Molecular Formula | C20H20O8 |
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Description
Epoxyquinol is an active substance produced by a fungus.
Specification
| IUPAC Name | (1R,2R,4R,6R,7S,11S,12R,13R,16R,18R,19S,22S)-7,19-dihydroxy-11,22-dimethyl-5,10,17,21-tetraoxaheptacyclo[11.7.2.02,8.02,12.04,6.014,20.016,18]docosa-8,14(20)-diene-3,15-dione |
| Canonical SMILES | CC1C2C3C(OC=C4C3(C(O1)C5=C2C(=O)C6C(C5O)O6)C(=O)C7C(C4O)O7)C |
| InChI | InChI=1S/C20H20O8/c1-4-7-8-9(13(23)16-15(27-16)12(8)22)19(26-4)20-6(3-25-5(2)10(7)20)11(21)14-17(28-14)18(20)24/h3-5,7,10-11,13-17,19,21,23H,1-2H3/t4-,5-,7-,10+,11-,13-,14+,15-,16+,17+,19+,20+/m0/s1 |
| InChI Key | HJZHVRIBNUVKQX-IBYRTHBISA-N |
Properties
| Appearance | Colorless Oil |
Reference Reading
1. Total synthesis of epoxyquinols A, B, and C and epoxytwinol A and the reactivity of a 2H-pyran derivative as the diene component in the Diels-Alder reaction
Mitsuru Shoji, Hiroki Imai, Makoto Mukaida, Ken Sakai, Hideaki Kakeya, Hiroyuki Osada, Yujiro Hayashi J Org Chem. 2005 Jan 7;70(1):79-91. doi: 10.1021/jo048425h.
Full details of two versions of the total synthesis of epoxyquinols A, B, and C and epoxytwinol A (RKB-3564D) are described. In the first-generation synthesis, the HfCl(4)-mediated diastereoselective Diels-Alder reaction of furan with Corey's chiral auxiliary has been developed. In the second-generation synthesis, a chromatography-free preparation of an iodolactone, by using acryloyl chloride as the dienophile in the Diels-Alder reaction of furan, and the lipase-mediated kinetic resolution of a cyclohexenol derivative have been developed. This second-generation synthesis is suitable for large-scale preparation. A biomimetic cascade reaction involving oxidation, 6pi-electrocyclization, and then Diels-Alder dimerization is the key reaction in the formation of the complex heptacyclic structure of epoxyquinols A, B, and C. Epoxytwinol A is synthesized by the cascade reaction composed of oxidation, 6pi-electrocyclization, and formal [4 + 4] cycloaddition reactions. A 2H-pyran, generated by oxidation/6pi-electrocyclization, acts as a good diene, reacting with several dienophiles to afford polycyclic compounds in one step. An azapentacyclic compound is synthesized by a similar cascade reaction composed of the four successive steps: oxidation, imine formation, 6pi-azaelectrocyclization, and Diels-Alder dimerization.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
