Milbemycin beta1

Base Information

• Chemical Name: Milbemycin beta1
• CAS No.: 51596-16-8
• Molecular Formula: C₃₂H₄₈O₇
• Molecular Weight: 544.729
• UNII: 112V7HX15Q
• Wikidata: Q27251215
• Mol file: 51596-16-8.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 beta1

Chemical Property:

• Boiling Point: 706.5°Cat760mmHg
• PKA: 12.50±0.70(Predicted)
• Flash Point: 221.7°C
• PSA: 94.45000
• Density: 1.16g/cm³
• LogP: 5.17190
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 544.34000387
• Heavy Atom Count: 39
• Complexity: 1010

Purity/Quality:

95% ^*data from raw suppliers

MILBEMYCIN BETA1 95.00% ^*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=C(C4(CC(C(=CC4C(=O)O3)C)OC)O)CO)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(/[C@@]4(C[C@@H](C(=C[C@H]4C(=O)O3)C)OC)O)\CO)C)\C)O[C@@H]1C

Technology Process of Milbemycin beta1

There total 47 articles about Milbemycin beta1 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: 75.0%

(+)-8'O-(tert-butyldimethylsilyl)milbemycin β1 (124553-46-4) → milbemycin β1 (51596-16-8)

Guidance literature:

With pyridine; hydrogen fluoride; In acetonitrile; Ambient temperature;

DOI:10.1016/S0040-4020(01)89182-1

Reference yield:

(-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone (116511-47-8) → milbemycin β1 (51596-16-8)

Guidance literature:

Multi-step reaction with 19 steps

1: 87 percent / tert-butyl-lithium / diethyl ether; tetrahydrofuran / 1 h / -78 °C

2: 1.) mCPBA; 2.) oxone / 1.) CH₂Cl₂, 0 deg C, 10 min; 2.) methanol/THF/H₂O, 0 deg C, 5 h

3: 1.) BH₃*DMS; 2.) aq. NaOH, H₂O₂ / 1.) THF, 0 deg C, --> room temp., 16 h; 2.) H₂O, 30 min

4: 45 percent / pyridinium-p-toluene sulphonate / benzene / 1 h / Heating; Dean-Stark conditions

5: 1.) n-butyllithium / 1.) hexanes, THF, -78 deg C, 15 min; 2.) -78 deg C, 1 h

6: 99 percent / mCPBA, sat. sodium hydrogencarbonate / CH₂Cl₂ / 0.75 h / 10 °C

7: 84 percent / 1.) tert-butyllithium / tetrahydrofuran / 1 h / -78 °C / 1.) -78 deg C, 10 min

8: 1.) 6percentsodium amalgam, Na₂HPO₄; 2.) DMAP / 1.) THF/MeOH, -40 deg C, 70 min; 2.) CH₂Cl₂, pyridine, room temp., 1 h

9: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / Heating

10: 76 percent / 1.) N-methyl-morpholine-N-oxide monohydrate, 4 Angstroem sieves / 2.) tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1.) room temp., 10 min; 2.) 5 min

11: NaO₂Cl, 2-methyl-2-butene, KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / Ambient temperature

12: NaOCH₃ / methanol / 0.5 h / Ambient temperature

13: triethylamine, 2-chloro-1-methylpyridinium iodide / acetonitrile / 3 h / Heating

14: 83 percent / N-methyl morpholine-N-oxide monohydrate, TPAP, 4 Angstroem sieves / CH₂Cl₂ / 1.) room temp., 10 min; 2.) 10 min

15: 92 percent / TFA / CH₂Cl₂ / Ambient temperature

16: 1.) triethylamine / 1.) CH₂Cl₂, room temp., 1.5 h; 2.) CH₂Cl₂, -78 deg C

17: 1.) 2-(phenylsulphonyl)-3-(p-nitrophenyl) oxaziridine; 2.) cerium(III) chloride heptahydrate, NaBH₄ / 1.) CDCl₃; 2.) methanol

18: 73 percent / silver(I) oxide / various solvent(s) / 36 h / Ambient temperature

19: 75 percent / 40percent aq. HF, pyridine / acetonitrile / Ambient temperature

With pyridine; dmap; Oxone; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; potassium dihydrogenphosphate; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; sodium amalgam; 2-methyl-but-2-ene; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen fluoride; 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; tert.-butyl lithium; sodium methylate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; silver(l) oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)89182-1

Reference yield:

5-hydroxymethyl-4-methoxy-1-methyl-1,3-cyclohexadiene (127785-50-6) → milbemycin β1 (51596-16-8)

Guidance literature:

Multi-step reaction with 28 steps

1: 98 percent / 4-dimethylaminopyridine, triethylamine / CH₂Cl₂ / 18 h / 0 °C

2: 88 percent / pyridinium-p-toluenesulphonate / benzene / 16 h / Heating; Dean-Stark conditions

3: 71 percent / osmium tetroxide, N-methylmorpholine-N-oxide monohydrate / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2 h / Ambient temperature

4: 43 percent / 1.) triethylamine; 2.) 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 0 °C / 1.) 10 min

5: 88 percent / potassium carbonate / methanol / 1 h / Ambient temperature

6: 100 percent / pyridinium-p-toluenesulphonate / CH₂Cl₂ / 0.33 h / Ambient temperature

7: 94 percent / acetic anhydride / 1 h / Heating

8: 1.) BH₃*DMS; 2.) aq. NaOH, H₂O₂ / 1.) THF, 10 deg C, --> room temp., 16 h; 2.) H₂O, 0 deg C, 1 h

9: 98 percent / palladium(II) chloride-acetonitrile complex / acetone / 7 h / Ambient temperature

10: 87 percent / tert-butyl-lithium / diethyl ether; tetrahydrofuran / 1 h / -78 °C

11: 1.) mCPBA; 2.) oxone / 1.) CH₂Cl₂, 0 deg C, 10 min; 2.) methanol/THF/H₂O, 0 deg C, 5 h

12: 1.) BH₃*DMS; 2.) aq. NaOH, H₂O₂ / 1.) THF, 0 deg C, --> room temp., 16 h; 2.) H₂O, 30 min

13: 45 percent / pyridinium-p-toluene sulphonate / benzene / 1 h / Heating; Dean-Stark conditions

14: 1.) n-butyllithium / 1.) hexanes, THF, -78 deg C, 15 min; 2.) -78 deg C, 1 h

15: 99 percent / mCPBA, sat. sodium hydrogencarbonate / CH₂Cl₂ / 0.75 h / 10 °C

16: 84 percent / 1.) tert-butyllithium / tetrahydrofuran / 1 h / -78 °C / 1.) -78 deg C, 10 min

17: 1.) 6percentsodium amalgam, Na₂HPO₄; 2.) DMAP / 1.) THF/MeOH, -40 deg C, 70 min; 2.) CH₂Cl₂, pyridine, room temp., 1 h

18: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / Heating

19: 76 percent / 1.) N-methyl-morpholine-N-oxide monohydrate, 4 Angstroem sieves / 2.) tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1.) room temp., 10 min; 2.) 5 min

20: NaO₂Cl, 2-methyl-2-butene, KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / Ambient temperature

21: NaOCH₃ / methanol / 0.5 h / Ambient temperature

22: triethylamine, 2-chloro-1-methylpyridinium iodide / acetonitrile / 3 h / Heating

23: 83 percent / N-methyl morpholine-N-oxide monohydrate, TPAP, 4 Angstroem sieves / CH₂Cl₂ / 1.) room temp., 10 min; 2.) 10 min

24: 92 percent / TFA / CH₂Cl₂ / Ambient temperature

25: 1.) triethylamine / 1.) CH₂Cl₂, room temp., 1.5 h; 2.) CH₂Cl₂, -78 deg C

26: 1.) 2-(phenylsulphonyl)-3-(p-nitrophenyl) oxaziridine; 2.) cerium(III) chloride heptahydrate, NaBH₄ / 1.) CDCl₃; 2.) methanol

27: 73 percent / silver(I) oxide / various solvent(s) / 36 h / Ambient temperature

28: 75 percent / 40percent aq. HF, pyridine / acetonitrile / Ambient temperature

With pyridine; dmap; dichloro bis(acetonitrile) palladium(II); Oxone; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; potassium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; sodium amalgam; 2-methyl-but-2-ene; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen fluoride; 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; tert.-butyl lithium; sodium methylate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; silver(l) oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic anhydride; acetone; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)89182-1

upstream raw materials:

(+)-8'O-(tert-butyldimethylsilyl)milbemycin β₁

(-)-(2S,4S,5S)-2-<(tert-butyldiphenylsilyloxy)methyl>-5-hydroxy-4-methylcyclohexanone

5-hydroxymethyl-4-methoxy-1-methyl-1,3-cyclohexadiene

5-<(tert-butyldiphenylsilyloxy)methyl>-4-methoxy-1-methyl-1,3-cyclohexadiene