Milbemycin A3

Base Information

• Chemical Name: Milbemycin A3
• CAS No.: 51596-10-2
• Deprecated CAS: 56197-00-3
• Molecular Formula: C₃₁H₄₄O₇
• Molecular Weight: 528.686
• European Community (EC) Number: 610-705-0,684-598-4
• UNII: C76Y8Z9GEX
• DSSTox Substance ID: DTXSID1058391
• Nikkaji Number: J34.159B
• Wikidata: Q27119774
• Metabolomics Workbench ID: 56196
• ChEMBL ID: CHEMBL2272396
• Mol file: 51596-10-2.mol

Synonyms:5-hydroxymilbemycin beta7;CL 301,423;CL 301423;Cydectin;Milbeknock;milbemectin;milbemycin A3;milbemycin A4;milbemycin alpha1;milbemycin alpha10;milbemycin alpha11;milbemycin alpha13;milbemycin alpha14;milbemycin alpha15;milbemycin alpha2;milbemycin alpha3;milbemycin alpha4;milbemycin alpha5;milbemycin alpha6;milbemycin alpha7;milbemycin alpha8;milbemycin alpha9;milbemycin B;milbemycin beta1;milbemycin beta12;milbemycin beta2;milbemycin beta3;milbemycin D;milbemycins;mixture of milbemycins A3 and A4;moxidectin

Chemical Property of Milbemycin A3

Chemical Property:

• Boiling Point: 725.5°Cat760mmHg
• PKA: 12.46±0.70(Predicted)
• Flash Point: 233.1°C
• PSA: 94.45000
• Density: 1.21g/cm³
• LogP: 4.53420
• Storage Temp.: 0-6°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 528.30870374
• Heavy Atom Count: 38
• Complexity: 1040

Purity/Quality:

95%, ^*data from raw suppliers

Milbemycin A3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)C)OC1C
• Isomeric SMILES: C[C@H]1CC[C@]2(C[C@@H]3C[C@H](O2)C/C=C(/C[C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)\C)O[C@@H]1C
• Recent ClinicalTrials: MESA Treatment for NK/T Cell Lymphoma
• Description: Milbemycin A3 is a member of a complex family of macrocyclic lactones that contain a characteristic spiroketal group produced from the fermentation of soil bacterium S. hygroscopicus subsp. aureolacrimosus. As a compound that potentiates glutamate and GABA-gated chloride-channel opening, milbemycin A3 is used as a nematocide and insecticide. The acaricidal and nematocidal activity of a mixture of milbemycin A3 and milbemycin A4 against adult spider mites, spider mite eggs, and C. elegans are reported at IC50 values of 5.3, 41.1, and 9.5 μg/ml.
• Uses: Milbemycins are a complex family of macrocyclic lactones containing a highly characteristic spiroketal group, produced by Streptomyces hydroscopicus subsp. aureolarcrimosus. Milbemycin A3 is a major member of a group of analogues containing a 25-methyl substituent. Milbemycin A3 is a highly selective and potent nematocide and insecticide. Like the closely related avermectins, milbemycins are thought to act on chloride-gated ion channels. Milbemycin A3 is widely used as a pesticides in agriculture. Milbemycin A3 (Milbemycin EP Impurity B) is an antibiotic with acaricidal activity.

Technology Process of Milbemycin A3

There total 14 articles about Milbemycin A3 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:

Benzoic acid (4S,6R,8R,9S)-2-((E)-(R)-3,5-dimethyl-6-oxo-hex-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester → Milbemectin (51596-10-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 63 percent / 1.) t-BuLi, HMPA / tetrahydrofuran / 1.) -78 deg C, 10 min; 2.) 1 h

2: 28 percent / sodium amalgame, Na₂HPO₄ / tetrahydrofuran; methanol / 0.75 h / -40 °C

3: 95 percent / pyridine, DMAP / CH₂Cl₂ / 0 - 25 °C

4: 88 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 - 25 °C

5: 95 percent / 1.) dimethylsulphoxide, oxalyl chloride, Et₃N / CH₂Cl₂ / -78 - 25 °C

6: sodium chlorite, aq. t-BuOH, Me₂C=CHMe, KH₂PO₄ / 1 h / Ambient temperature

7: sodium methoxide / methanol

8: 2,4,6-trichlorobenzoyl chloride, 4-pyrrolidino-pyridine, Et₃N / CH₂Cl₂ / Heating

9: 79 percent / TPAP, 4A molecular sieves / CH₂Cl₂ / Ambient temperature

10: 85 percent / ZnCl₂, Et₃N / CH₂Cl₂ / 6 h / 0 °C

11: CH₂Cl₂ / 2 h / -78 °C

12: HF, pyridine / acetonitrile / 60 h / Ambient temperature

13: 1.) 2-(phenylsulphonyl)-3-(p-nitrophenyl)oxaziridine; 2.) NaBH₄, CeCl₃ / 1.) CDCl₃, rt., 2 h; 2.) MeOH, 0 deg C, 20 min

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; potassium dihydrogenphosphate; sodium amalgam; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium methylate; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; triethylamine; zinc(II) chloride; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60158-2

Reference yield:

(3aS,4R,6S,7R,7aR)-3a,7-Dihydroxy-3-[(2E,6E)-(R)-8-((2R,4S,6R,8R,9S)-4-hydroxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-4,6-dimethyl-octa-2,6-dien-(E)-ylidene]-6-methyl-octahydro-benzofuran-4-carboxylic acid → Milbemectin (51596-10-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 2,4,6-trichlorobenzoyl chloride, 4-pyrrolidino-pyridine, Et₃N / CH₂Cl₂ / Heating

2: 79 percent / TPAP, 4A molecular sieves / CH₂Cl₂ / Ambient temperature

3: 85 percent / ZnCl₂, Et₃N / CH₂Cl₂ / 6 h / 0 °C

4: CH₂Cl₂ / 2 h / -78 °C

5: HF, pyridine / acetonitrile / 60 h / Ambient temperature

6: 1.) 2-(phenylsulphonyl)-3-(p-nitrophenyl)oxaziridine; 2.) NaBH₄, CeCl₃ / 1.) CDCl₃, rt., 2 h; 2.) MeOH, 0 deg C, 20 min

With pyridine; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine; 4-pyrrolidin-1-ylpyridine; triethylamine; zinc(II) chloride; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60158-2

Reference yield:

C31H46O7 (1053268-82-8) → Milbemectin (51596-10-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / TPAP, 4A molecular sieves / CH₂Cl₂ / Ambient temperature

2: 85 percent / ZnCl₂, Et₃N / CH₂Cl₂ / 6 h / 0 °C

3: CH₂Cl₂ / 2 h / -78 °C

4: HF, pyridine / acetonitrile / 60 h / Ambient temperature

5: 1.) 2-(phenylsulphonyl)-3-(p-nitrophenyl)oxaziridine; 2.) NaBH₄, CeCl₃ / 1.) CDCl₃, rt., 2 h; 2.) MeOH, 0 deg C, 20 min

With pyridine; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen fluoride; 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine; triethylamine; zinc(II) chloride; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60158-2

upstream raw materials:

C₃₁H₄₆O₇

Downstream raw materials:

5-O-methylmilbemycin A3

5-ketomilbemycin A₃ 5-oxime

Refernces