3-Ethoxy-spinosyn L 17-pseudoaglycone
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| Category | Others |
| Catalog number | BBF-04249 |
| CAS | |
| Molecular Weight | 618.80 |
| Molecular Formula | C35H54O9 |
| Purity | >95% by HPLC |
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Description
It is an acid degradation product produced by selective hydrolysis of the more labile forosamine saccharide in the 17-position of 3-ethoxy-5,6-dihydrospinosyn J, the minor component of the commercial product, spinetoram. It has only weak activity as an insecticide.
Specification
| Storage | Store at -20°C |
| IUPAC Name | (2S,3aR,5aS,5bS,9S,13S,14R,16aS,16bS)-2-(((2R,3R,4R,5S,6S)-4-ethoxy-3,5-dimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-9-ethyl-13-hydroxy-4,14-dimethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15-dione |
| Canonical SMILES | O=C1C2=C[C@]3([H])[C@](C=C(C)[C@@]4([H])[C@@]3([H])C[C@H](O[C@]5([H])O[C@@H](C)[C@H](OC)[C@@H](OCC)[C@H]5OC)C4)([H])[C@]2([H])CC(O[C@@H](CC)CCC[C@H](O)[C@H]1C)=O |
| InChI | InChI=1S/C35H54O9/c1-8-21-11-10-12-29(36)19(4)31(38)28-16-26-24(27(28)17-30(37)43-21)13-18(3)23-14-22(15-25(23)26)44-35-34(40-7)33(41-9-2)32(39-6)20(5)42-35/h13,16,19-27,29,32-36H,8-12,14-15,17H2,1-7H3/t19-,20+,21+,22-,23+,24-,25-,26-,27+,29+,32+,33-,34-,35+/m1/s1 |
| InChI Key | QTDUHVNIJHBCHA-UABBEYQPSA-N |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Parasites |
Reference Reading
1. Conversion of spinosyn A and spinosyn D to their respective 9- and 17-pseudoaglycones and their aglycones
J W Paschal, H A Kirst, L C Creemer J Antibiot (Tokyo) . 1998 Aug;51(8):795-800. doi: 10.7164/antibiotics.51.795.
Forosamine at the 17-position of spinosyns A and D was hydrolyzed under mild acidic conditions to give the corresponding 17-pseudoaglycones. The tri-O-methylrhamnose at the 9-position of the 17-pseudoaglycone of spinosyn A was hydrolyzed under more vigorous acidic conditions to give the aglycone of spinosyn A. However, these conditions led to decomposition of the 17-pseudoaglycone of spinosyn D, presumably due to more facile protonation of the 5,6-double bond to produce a tertiary carbonium ion which undergoes further rearrangements. Spinosyns J and L (3'-O-demethyl spinosyn A and D, respectively) obtained from fermentation of biosynthetically-blocked mutant strains of Saccharopolyspora spinosa, were oxidized to give the corresponding 3'-keto-derivatives and the resultant keto-sugars were then beta-eliminated under basic conditions to give the 9-pseudoaglycones of spinosyns A and D respectively. Forosamine at the 17-position of the 9-pseudoaglycone of spinosyn D was then readily hydrolyzed to yield the aglycone of spinosyn D.
2. Spinosyn g: proof of structure by semisynthesis
Paul R Graupner, Jacek Martynow, Peter B Anzeveno J Org Chem . 2005 Mar 18;70(6):2154-60. doi: 10.1021/jo048173k.
[reaction: see text] Spinosyn G was isolated in the late 1980s as a minor component from the broth of our potent, fermentation-derived insecticide spinosad. Its structure was then tentatively identified as 5' '-epispinosyn A (3) on the basis of (1)H and (13)C NMR data, but the 4' '-epi compound 4 could not be conclusively ruled out with the data available. Described herein are unambiguous syntheses of both 3 and 4, whereby 3 was proved identical to the natural product. Compound 4 was prepared from intact spinosyn A by a novel F-TEDA-promoted oxidative deamination to the 4' '-ketone 5, stereoselective reduction to the equatorial alcohol 6, and nitrogen incorporation via the axial azide 7. Compound 3 was obtained by coupling spinosyn A 17-pseudoaglycone (9) with the N-protected dihydropyran 16 derived from methyl l-ossaminide (14). This gave an approximately 2:1 mixture of anomeric products 17 with the desired equatorial glycoside predominating, which was then converted to 3 by N-deprotection and methylation.
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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 ╳
