Nemadectin

Base Information

• Chemical Name: Nemadectin
• CAS No.: 102130-84-7
• Molecular Formula: C36H52 O8
• Molecular Weight: 612.804
• UNII: 1Y8VJ1G3TY
• DSSTox Substance ID: DTXSID20883099
• Nikkaji Number: J326.623K
• Wikidata: Q27253169
• NCI Thesaurus Code: C90750
• Metabolomics Workbench ID: 116633
• ChEMBL ID: CHEMBL2103942
• Mol file: 102130-84-7.mol

Synonyms:MilbemycinB, 5-O-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-hydroxy-,[6R,23S,25S(E)]- (9CI);Spiro[11,15-methano-2H,13H,17H-furo[4,3,2-pq][2,6]benzodioxacyclooctadecin-13,2'-[2H]pyran],milbemycin B deriv.; Antibiotic LL-F 28249a; Antibiotic S 541A; CL 287088; F 28249a; L 669437; LL-F 28249a; Megatop; Nemadectin; Nemadectina

Chemical Property of Nemadectin

Chemical Property:

• Boiling Point: 786°Cat760mmHg
• PKA: 12.46±0.70(Predicted)
• Flash Point: 241.9°C
• PSA: 114.68000
• Density: 1.19g/cm³
• LogP: 5.08740
• XLogP3: 4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 612.36621861
• Heavy Atom Count: 44
• Complexity: 1240

Purity/Quality:

98%Min ^*data from raw suppliers

Nemadectin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=CCC2CC(CC3(O2)CC(C(C(O3)C(=CC(C)C)C)C)O)OC(=O)C4C=C(C(C5C4(C(=CC=C1)CO5)O)O)C)C
• Isomeric SMILES: C[C@@H]\1C/C(=C/C[C@@H]2C[C@@H](C[C@@]3(O2)C[C@@H]([C@@H]([C@H](O3)/C(=C/C(C)C)/C)C)O)OC(=O)[C@@H]4C=C([C@H]([C@@H]5[C@]4(/C(=C/C=C1)/CO5)O)O)C)/C
• Description: The nemadectins are fermentation products of Streptomyces cyaneogriseus noncyanogenus. Structurally, the nemadectins lack a disaccharide group at C-13 but differ from the milbemycins proper because they contain a trisubstituted double bond at C-26 in their side chains.
• Uses: Nemadectin is a potent antiparasitic macrolide lactone. Nemadectin is the dominant member of a class of milbemycins bearing unsaturated longer chain groups at the 25-position. Nemadectin shows pronounced nematocidal and insecticidal activity. Nemadectin is the starting material for moxidectin, a commercial anthelmintic.

Technology Process of Nemadectin

There total 6 articles about Nemadectin 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: 95.2%

5-(4-chlorophenoxyacetyl)oxynemadectin → nemadectin α (102130-84-7)

Guidance literature:

With methanol; sodium hydroxide; In dichloromethane; at 0 - 5 ℃; for 1h;

Reference yield:

5-oxo(4-nitrobenzoyl)nimoxetine → nemadectin α (102130-84-7)

Guidance literature:

With methanol; sodium hydroxide; In dichloromethane; at 0 - 5 ℃; for 1h;

Reference yield:

5-oxo(4-nitrobenzoyl)-23-oxonemadectin (133120-37-3) → nemadectin α (102130-84-7)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; sodium tetrahydroborate / 1 h / 0 - 5 °C

2: methanol; sodium hydroxide / dichloromethane / 1 h / 0 - 5 °C

With methanol; sodium tetrahydroborate; sodium hydroxide; In dichloromethane;

upstream raw materials:

5-oxo(4-nitrobenzoyl)-23-oxonemadectin

Downstream raw materials:

C₃₉H₅₆O₉

C₃₈H₅₄O₁₀

C₄₄H₆₄O₁₁

C₄₁H₅₅Cl₃O₁₁

Refernces