Technology Process of (4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-2-(phenylsulfonyl)-8-(triethylsiloxy)-3-nonanone
There total 24 articles about (4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-2-(phenylsulfonyl)-8-(triethylsiloxy)-3-nonanone which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
Dess-Martin periodane;
In
dichloromethane;
DOI:10.1021/ja990384x
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 0.33 h / 0 °C
1.2: 89 percent / tetrahydrofuran; toluene / 0.33 h / 0 °C
2.1: 99 percent / (DHQ)2PYR; OsO4; K3Fe(CN)6 / K2CO3 / H2O; 2-methyl-propan-2-ol / 0 °C
3.1: 636 mg / imidazole / tetrahydrofuran / 5 h
4.1: 439 mg / DMAP; imidazole / dimethylformamide / 5 h
5.1: 79 percent / Dibal-H / tetrahydrofuran; hexane / 1 h / -40 °C
6.1: 89 percent / tetra-n-propylammonium perruthenate; NMO; 4A MS / CH2Cl2 / 1 h
7.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
7.2: 76 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C
8.1: 97 percent / Dess-Martin periodinane / CH2Cl2 / 1 h
With
1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; potassium hexacyanoferrate(III);
potassium carbonate;
In
tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1.1: Metallation / 1.2: Wittig olefination / 2.1: hydroxylation / 3.1: silylation / 4.1: silylation / 5.1: reductive deacylation / 6.1: Oxidation / 7.1: Metallation / 7.2: Addition / 8.1: Oxidation;
DOI:10.1021/ja993487o
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 99 percent / (DHQ)2PYR; OsO4; K3Fe(CN)6 / K2CO3 / H2O; 2-methyl-propan-2-ol / 0 °C
2.1: 636 mg / imidazole / tetrahydrofuran / 5 h
3.1: 439 mg / DMAP; imidazole / dimethylformamide / 5 h
4.1: 79 percent / Dibal-H / tetrahydrofuran; hexane / 1 h / -40 °C
5.1: 89 percent / tetra-n-propylammonium perruthenate; NMO; 4A MS / CH2Cl2 / 1 h
6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
6.2: 76 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C
7.1: 97 percent / Dess-Martin periodinane / CH2Cl2 / 1 h
With
1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); diisobutylaluminium hydride; Dess-Martin periodane; potassium hexacyanoferrate(III);
potassium carbonate;
In
tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: hydroxylation / 2.1: silylation / 3.1: silylation / 4.1: reductive deacylation / 5.1: Oxidation / 6.1: Metallation / 6.2: Addition / 7.1: Oxidation;
DOI:10.1021/ja993487o
