(+)-8'O-(tert-butyldimethylsilyl)-5-desmethoxy-3,4-dihydro-5-oxo-4-(phenylselenenyl)milbemycin β₁

Base Information

• Chemical Name: (+)-8'O-(tert-butyldimethylsilyl)-5-desmethoxy-3,4-dihydro-5-oxo-4-(phenylselenenyl)milbemycin β₁
• CAS No.: 124553-42-0
• Molecular Formula: C₄₃H₆₄O₇SeSi
• Molecular Weight: 800.022

Synonyms:

Chemical Property of (+)-8'O-(tert-butyldimethylsilyl)-5-desmethoxy-3,4-dihydro-5-oxo-4-(phenylselenenyl)milbemycin β₁

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-8'O-(tert-butyldimethylsilyl)-5-desmethoxy-3,4-dihydro-5-oxo-4-(phenylselenenyl)milbemycin β₁

There total 32 articles about (+)-8'O-(tert-butyldimethylsilyl)-5-desmethoxy-3,4-dihydro-5-oxo-4-(phenylselenenyl)milbemycin β₁ 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:

(+)-<2R,4E,6(2R,4S,6S,8R,9S)>-6-(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-2,4-dimethyl-4-hexenal (115031-05-5) → (+)-8'O-(tert-butyldimethylsilyl)-5-desmethoxy-3,4-dihydro-5-oxo-4-(phenylselenenyl)milbemycin β1 (124553-42-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 83 percent / t-butyl lithium / tetrahydrofuran / -78 °C

2: sodium amalgam, Na₂HPO₄ / tetrahydrofuran; methanol / -40 °C

3: 27 percent / py, DMAP

4: 91 percent / TBAF / tetrahydrofuran / Heating

5: 76 percent / tetra-n-propylammonium perruthenate, NMO, 4 angstroem ground sieves / CH₂Cl₂

6: sodium chlorite, 2-methyl-2-butene, KH₂PO₄ / 2-methyl-propan-2-ol; H₂O

7: sodium methoxide / methanol

8: 2-chloro-1-methyl-pyridinium iodide, Et₃N / acetonitrile / Heating

9: 83 percent / tetra-n-propylammonium perruthenate, NMO, 4 angstroem ground sieves / CH₂Cl₂

10: 92 percent / trifluoroacetic acid / CH₂Cl₂

11: Et₃N / CH₂Cl₂ / Ambient temperature

12: Et₃N / CH₂Cl₂ / -78 °C

With pyridine; dmap; sodium chlorite; disodium hydrogenphosphate; potassium dihydrogenphosphate; sodium amalgam; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; tert.-butyl lithium; sodium methylate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)99203-7

Reference yield:

(+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-10-benzoyloxy-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecane-7-methanol (127785-60-8) → (+)-8'O-(tert-butyldimethylsilyl)-5-desmethoxy-3,4-dihydro-5-oxo-4-(phenylselenenyl)milbemycin β1 (124553-42-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 76 percent / tetra-n-propylammonium perruthenate, NMO, 4 angstroem ground sieves / CH₂Cl₂

2: sodium chlorite, 2-methyl-2-butene, KH₂PO₄ / 2-methyl-propan-2-ol; H₂O

3: sodium methoxide / methanol

4: 2-chloro-1-methyl-pyridinium iodide, Et₃N / acetonitrile / Heating

5: 83 percent / tetra-n-propylammonium perruthenate, NMO, 4 angstroem ground sieves / CH₂Cl₂

6: 92 percent / trifluoroacetic acid / CH₂Cl₂

7: Et₃N / CH₂Cl₂ / Ambient temperature

8: Et₃N / CH₂Cl₂ / -78 °C

With sodium chlorite; potassium dihydrogenphosphate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; 2-chloro-1-methyl-pyridinium iodide; sodium methylate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)99203-7

Reference yield:

(+)-<2R,5E<2E,4R,6E,8(2R,4S,6S,8R,9S)>,6S,8S,9S,11S>-5-<(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-4,6-dimethyl-2,6-octadienylidene>-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-1,3-dioxaspiro<5.5>undecan-8-ol (124553-37-3) → (+)-8'O-(tert-butyldimethylsilyl)-5-desmethoxy-3,4-dihydro-5-oxo-4-(phenylselenenyl)milbemycin β1 (124553-42-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / TBAF / tetrahydrofuran / Heating

2: 76 percent / tetra-n-propylammonium perruthenate, NMO, 4 angstroem ground sieves / CH₂Cl₂

3: sodium chlorite, 2-methyl-2-butene, KH₂PO₄ / 2-methyl-propan-2-ol; H₂O

4: sodium methoxide / methanol

5: 2-chloro-1-methyl-pyridinium iodide, Et₃N / acetonitrile / Heating

6: 83 percent / tetra-n-propylammonium perruthenate, NMO, 4 angstroem ground sieves / CH₂Cl₂

7: 92 percent / trifluoroacetic acid / CH₂Cl₂

8: Et₃N / CH₂Cl₂ / Ambient temperature

9: Et₃N / CH₂Cl₂ / -78 °C

With sodium chlorite; potassium dihydrogenphosphate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; sodium methylate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)99203-7

upstream raw materials:

Phenylselenyl chloride

t-butyldimethylsiyl triflate

(+)-5-desmethoxy-3,4S-dihydro-5-oxomilbemycin β₁

(+)-<2R,4E,6(2R,4S,6S,8R,9S)>-6-(4-benzoyloxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undecan-2-yl)-2,4-dimethyl-4-hexenal

Downstream raw materials:

(+)-milbemycin β₁

milbemycin β₁

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