(+)-5-O-desmethyl-3,4S-dihydromilbemycin β₁ 7,8'-R-benzylidene acetal

Base Information

• Chemical Name: (+)-5-O-desmethyl-3,4S-dihydromilbemycin β₁ 7,8'-R-benzylidene acetal
• CAS No.: 124553-40-8
• Molecular Formula: C₃₈H₅₂O₇
• Molecular Weight: 620.827

Synonyms:(+)-5-O-desmethyl-3,4S-dihydromilbemycin β₁ 7,8'-R-benzylidene acetal

Chemical Property of (+)-5-O-desmethyl-3,4S-dihydromilbemycin β₁ 7,8'-R-benzylidene acetal

Chemical Property:

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Technology Process of (+)-5-O-desmethyl-3,4S-dihydromilbemycin β₁ 7,8'-R-benzylidene acetal

There total 26 articles about (+)-5-O-desmethyl-3,4S-dihydromilbemycin β₁ 7,8'-R-benzylidene acetal 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,5S(E),6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethenyl>-1,3-dioxaspiro<5.5>undecan-8-ol (115030-97-2,124600-50-6) → (+)-5-O-desmethyl-3,4S-dihydromilbemycin β1 7,8'-R-benzylidene acetal (124553-40-8)

Guidance literature:

Multi-step reaction with 8 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

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; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;

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

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) → (+)-5-O-desmethyl-3,4S-dihydromilbemycin β1 7,8'-R-benzylidene acetal (124553-40-8)

Guidance literature:

Multi-step reaction with 8 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

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; 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) → (+)-5-O-desmethyl-3,4S-dihydromilbemycin β1 7,8'-R-benzylidene acetal (124553-40-8)

Guidance literature:

Multi-step reaction with 4 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

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; In methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;

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

upstream raw materials:

(2R,6S,7R,9S,10S)-10-Hydroxy-5-[(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]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid

(+)-<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

C₆₁H₇₈O₈Si

(+)-(2R,5S(E),6S,8S,9S,11S)-11-<(tert-butyldiphenylsilyloxy)methyl>-9-methyl-2-phenyl-5-<2-(phenylsulphonyl)ethenyl>-1,3-dioxaspiro<5.5>undecan-8-ol

Downstream raw materials:

(+)-5-desmethoxy-3,4S-dihydro-5-oxomilbemycin β₁ 7,8'-R-benzylidene acetal

milbemycin β₁

(+)-milbemycin β₁

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

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