Spinosyn A 17-pseudoaglycone

Base Information

• Chemical Name: Spinosyn A 17-pseudoaglycone
• CAS No.: 131929-68-5
• Molecular Formula: C₃₃H₅₀O₉
• Molecular Weight: 590.755
• DSSTox Substance ID: DTXSID001029382
• Nikkaji Number: J1.705.091E
• Wikidata: Q76422007
• Mol file: 131929-68-5.mol

Synonyms:Spinosyn A 17-pseudoaglycone;131929-68-5;(1S,2R,5S,7R,9R,10S,14R,15S,19S)-19-Ethyl-15-hydroxy-14-methyl-7-[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy-20-oxatetracyclo[10.10.0.02,10.05,9]docosa-3,11-diene-13,21-dione;A 83543A pseudoglycone;DTXSID001029382;2',3',4'-O-methyl-rhamnosyl tetracyclic spinosyn pseudoaglycone;(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-{[(3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy}-1H,2H,3H,3aH,5aH,5bH,6H,7H,9H,10H,11H,12H,13H,14H,15H,16aH,16bH-as-indaceno[3,2-d]oxacyclododecane-7,15-dione;9-ethyl-13-hydroxy-14-methyl-2-(3,4,5-trimethoxy-6-methyltetrahydro-2H- pyran-2-yloxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H- as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)- dione

Chemical Property of Spinosyn A 17-pseudoaglycone

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 590.34548317
• Heavy Atom Count: 42
• Complexity: 1030

Purity/Quality:

98% ^*data from raw suppliers

Spinosyn A 17-pseudoaglycone ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1CCCC(C(C(=O)C2=CC3C4CC(CC4C=CC3C2CC(=O)O1)OC5C(C(C(C(O5)C)OC)OC)OC)C)O
• Isomeric SMILES: CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3[C@@H]2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O
• Description: Spinosyn A 17-pseudoaglycone is a pseudoaglycone form of the macrocyclic lactone insecticide spinosyn A . Unlike spinosyn A, spinosyn A 17-pseudoaglycone is not lethal to tobacco budworm (H. virescens) neonate larvae (LC50 = >64 ppm).
• Uses: Spinosyn A 17-pseudoaglycone is an acid degradation product produced by selective hydrolysis of the more labile forosamine saccharide in the 17-position of spinosyn A, the major component of the commercial product, Spinosad. Spinosyn A 17-pseudoaglycone is only weakly active as an insecticide as the forosamine moiety is considered essential for potent activity. Despite the importance of spinosyns as agro-chemical insecticides and more recently as animal health products, there are few published reports of the biological activity or the levels of spinosyn A 17-pseudoaglycone in animals or in the environment.

Technology Process of Spinosyn A 17-pseudoaglycone

There total 48 articles about Spinosyn A 17-pseudoaglycone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

(3S,3aR,5aS,7S,8aR,8bS)-2-[(2R,3S,7S)-3-(tert-butyldiphenylsiloxy)-7-hydroxy-2-methylnonanoyl]-7-[(6-deoxy-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-3,3a,5a,6,7,8,8a,8b-octahydro-as-indacene-3-acetic acid κ-lactone (204381-45-3) → (2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione (131929-68-5)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 24h;

DOI:10.1021/ja974010k

Reference yield: 91.0%

C41H58O10 (1011242-84-4) → (2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione (131929-68-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 ℃; for 5h; pH=7;

DOI:10.1021/jacs.6b07585

Reference yield: 90.0%

spinosyn A (131929-60-7) → (2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione (131929-68-5)

Guidance literature:

With sulfuric acid; In water; at 80 - 90 ℃; for 24h;

DOI:10.1021/jo048173k

upstream raw materials:

(3S,3aR,5aS,7S,8aR,8bS)-2-[(2R,3S,7S)-3-(tert-butyldiphenylsiloxy)-7-hydroxy-2-methylnonanoyl]-7-[(6-deoxy-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-3,3a,5a,6,7,8,8a,8b-octahydro-as-indacene-3-acetic acid κ-lactone

spinosyn A

methyl 4-formylbutanoate

(S)-5-Hydroxy-heptanoic acid methyl ester

Downstream raw materials:

spinosyn A

Refernces

• 1、 Lai, Qin,Li, Zeng-Xia,Liu, Li-Jun,Liu, Su-You,Luo, Zhi-Yong,Ma, Da-You,Peng, Kun-Jian,Wang, Long-Long. "Synthesis and anti-OXPHOS, antitumor activities of DLC modified spinosyn derivatives". . . Retrieved 2020/03/10.
• 2、 Zhang, Kai,Liu, Shenglan,Liu, Anjun,Chai, Hongxin,Li, Jiarong,Lamusi. "A semisynthesis of 3′-O-ethyl-5,6-dihydrospinosyn J based on the spinosyn A aglycone". . p. 2603 - 2609. Retrieved 2018/01/17.