Dihydrospinosyn A aglycone

Dihydrospinosyn A aglycone

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Dihydrospinosyn A aglycone
Category Others
Catalog number BBF-04237
CAS 727695-12-7
Molecular Weight 404.54
Molecular Formula C24H36O5
Purity >95% by HPLC

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Description

It is an acid degradation product produced by hydrolysis of both saccharide groups of 3-ethoxy-5,6-dihydrospinosyn J, the major component of the commercial insecticide, spinetoram. It has only weak activity as an insecticide and the saccharides are considered essential for potent activity. It is commonly used as an insecticide for agricultural chemicals.

Specification

Synonyms (2R,3aR,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-2,3,3a,4,5,5a,5b,6,9,10,11,12,13,14,16a,16b-hexadecahydro-2,13-dihydroxy-14-methyl-1H-as-indaceno[3,2-d]oxacyclododecin-7,15-dione
Storage Store at -20°C
IUPAC Name (1S,2R,5R,7R,9R,10S,14R,15S,19S)-19-ethyl-7,15-dihydroxy-14-methyl-20-oxatetracyclo[10.10.0.02,10.05,9]docos-11-ene-13,21-dione
Canonical SMILES CCC1CCCC(C(C(=O)C2=CC3C(C2CC(=O)O1)CCC4C3CC(C4)O)C)O
InChI InChI=1S/C24H36O5/c1-3-16-5-4-6-22(26)13(2)24(28)21-11-19-17(20(21)12-23(27)29-16)8-7-14-9-15(25)10-18(14)19/h11,13-20,22,25-26H,3-10,12H2,1-2H3/t13-,14-,15-,16+,17-,18-,19-,20+,22+/m1/s1
InChI Key ILUFDLFVFFUVQX-MRAVEKNJSA-N
Source Semi-synthetic

Properties

Appearance White Solid
Antibiotic Activity Spectrum Parasites
Boiling Point 626.8±55.0°C (Predicted)
Density 1.18±0.1 g/cm3 (Predicted)
Solubility Soluble in Ethanol, Methanol, DMF, DMSO

Reference Reading

1. A semisynthesis of 3'- O-ethyl-5,6-dihydrospinosyn J based on the spinosyn A aglycone
Anjun Liu, Hongxin Chai, Shenglan Liu, Jiarong Li, Kai Zhang, Lamusi A Beilstein J Org Chem . 2017 Dec 6;13:2603-2609. doi: 10.3762/bjoc.13.257.
Spinetoram, a mixture of 3'-O-ethyl-5,6-dihydrospinosyn J (XDE-175-J, major component) and 3'-O-ethylspinosyn L (XDE-175-L, minor component), is a novel kind of green and efficient insecticide with a broad range of action against various insects. Nowadays, spinetoram is widely used in agriculture and food storage. This work reports a 7-step semisynthesis of 3'-O-ethyl-5,6-dihydrospinosyn J from spinosyn A aglycone. The C9-OH and C17-OH of the aglycone are successively connected to 3-O-ethyl-2,4-di-O-methylrhamnose and D-forosamine after selective protection and deprotection steps. Then, with 10% Pd/C as catalyst, the 5,6-double bond of the macrolide was selectively reduced to afford 3'-O-ethyl-5,6-dihydrospinosyn J. In addition, the 3-O-ethyl-2,4-di-O-methylrhamnose is synthesized from rhamnose which is available commercially, while the D-forosamine and aglycone are obtained via the hydrolysis of spinosyn A. High yields were obtained in each step, and all intermediates in the synthesis were characterized by1H NMR,13C NMR and MS techniques. This study can be helpful for developing an efficient chemical synthesis of spinetoram, and it also offers opportunities to synthesize spinosyn analogues and rhamnose derivatives.

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