(4R)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B₁a aglycone

Base Information

• Chemical Name: (4R)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B₁a aglycone
• CAS No.: 135419-83-9
• Molecular Formula: C₄₆H₆₈O₈SeSi₂
• Molecular Weight: 884.172

Synonyms:

Chemical Property of (4R)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B₁a aglycone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B₁a aglycone

There total 78 articles about (4R)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B₁a aglycone 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: 47.0%

Phenylselenyl chloride (5707-04-0) + 5-dehydro-3-hydro-5,7,13-tri-O-(trimethylsilyl)avermectin B1a aglycone (135419-93-1) → (4S)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B1a aglycone (135419-83-9,135502-85-1) + (4R)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B1a aglycone (135419-83-9,135502-85-1)

Guidance literature:

In dichloromethane; at -78 ℃; for 2h;

Reference yield: 47.0%

Phenylselenyl chloride (5707-04-0) + 5-dehydro-3-hydro-5,7,13-tri-O-(trimethylsilyl)avermectin B1a aglycone (135419-93-1) → (4S)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B1a aglycone (135419-83-9,135502-85-1) + (4R)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B1a aglycone (135419-83-9,135502-85-1)

Guidance literature:

In dichloromethane; at -78 ℃; for 2h;

Reference yield:

(1S,2S,3S,5S,6S)-3-<(tert-butyldiphenylsilyloxy)methyl>-5-methyl-2-<1-methylene-3-(phenylthio)propyl>-7-oxabicyclo<4.1.0>heptan-2-ol (131414-04-5) → (4S)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B1a aglycone (135419-83-9,135502-85-1)

Guidance literature:

Multi-step reaction with 20 steps

1: 88 percent / oxone, pH 4 aqueous buffer / tetrahydrofuran; methanol / 3.5 h / Ambient temperature

2: 80 percent / 15percent aq. H₂SO₄ / tetrahydrofuran / 12 h / 60 °C

3: 91 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

4: 86 percent / NEt₃ / CH₂Cl₂ / 0.25 h / Ambient temperature

5: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) THF, -35 deg C, 20 min, 2.) -78 deg C -> RT

6: 79 percent / NaBH₄ / methanol / Ambient temperature

7: 1.) borane methyl sulphide complex, 2.) H₂O₂, NaOH / 1.) THF, RT, 64 h, 2.) 0 deg C -> RT

8: 84 percent / toluene-p-sulphonyl chloride, pyridine / 14 h / Ambient temperature

9: 1.) tert-BuLi / 1.) hexane, THF, -78 deg C, 10 min, 2.) -78 deg C, 10 min

10: 93 percent / 80percent m-chloroperbenzoic acid (mCPBA) / CH₂Cl₂ / 0.25 h / Ambient temperature

11: 80 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 3.5 h / Ambient temperature

12: 1.) tert-BuLi / 1.) pentane, THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h

13: 34 percent / 6percent Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 2 h / -40 °C

14: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 36 h / Heating

15: tris(triphenylphosphine)ruthenium(II) chloride / benzene; CH₂Cl₂ / 48 h / Ambient temperature

16: 32 percent / NaClO₂, 2-methylbut-2-ene / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

17: 47 percent / 2-chloro-1-methylpyridinium iodide, NEt₃ / acetonitrile / 4 h / Heating

18: 61 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / Ambient temperature

19: 88 percent / NEt₃ / CH₂Cl₂ / 4 h / 0 °C

20: 44 percent / CH₂Cl₂ / 2 h / -78 °C

With pyridine; 1H-imidazole; Oxone; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; oxalyl dichloride; tris(triphenylphosphine)ruthenium(II) chloride; dimethylsulfide borane complex; pH 4 aqueous buffer; sulfuric acid; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; tert.-butyl lithium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;

upstream raw materials:

Phenylselenyl chloride

5-dehydro-3-hydro-5,7,13-tri-O-(trimethylsilyl)avermectin B₁a aglycone

(1E,3S,4S)-1-bromo-2,4-dimethylhexa-1,5-dien-3-ol

(1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene

Downstream raw materials:

avermectin B₁a

(4S)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-avermectin B₁a aglycone

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