Technology Process of (R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-[(2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-yl]-3-methyl-butan-2-one
There total 14 articles about (R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-[(2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-yl]-3-methyl-butan-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 96 percent / TiCl4 / benzene / 0.5 h / 0 °C
2.1: 85 percent / mCPBA / CH2Cl2 / 20 °C
3.1: 76 percent / BF3OMe2 / 3 h / 90 °C
4.1: 99 percent / K2CO3 / acetone / 40 h / 20 °C
5.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C
5.2: Ti(i-PrO)3Cl / tetrahydrofuran / 1 h / -78 - -40 °C
5.3: 58 percent / tetrahydrofuran / 3 h / -78 - -40 °C
6.1: Me4NBH(OAc)3 / acetonitrile; acetic acid / 16 h / -30 - 20 °C
7.1: 93 percent / 18 h / 20 °C
8.1: 83 percent / DDQ; 4 Angstroem molecular sieves / CH2Cl2; H2O; various solvent(s) / 0.5 h
9.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 1.75 h / -78 - 0 °C
10.1: LiOH / diethyl ether / 0.25 h / 20 °C
10.2: 85 percent / diethyl ether / 4 h / 20 °C
11.1: 84 percent / aq. HCl / methanol / 6 h / 20 °C
With
hydrogenchloride; lithium hydroxide; boron trifluoride dimethyl etherate; oxalyl dichloride; 4 A molecular sieve; titanium tetrachloride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; acetone; acetonitrile; benzene;
1.1: Friedel-Crafts acylation / 2.1: Bayer-Villiger oxidation / 3.1: ortho-Fries rearrangement / 9.1: Swern oxidation / 10.1: Horner-Wadsworth-Emmons reaction / 10.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 85 percent / mCPBA / CH2Cl2 / 20 °C
2.1: 76 percent / BF3OMe2 / 3 h / 90 °C
3.1: 99 percent / K2CO3 / acetone / 40 h / 20 °C
4.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C
4.2: Ti(i-PrO)3Cl / tetrahydrofuran / 1 h / -78 - -40 °C
4.3: 58 percent / tetrahydrofuran / 3 h / -78 - -40 °C
5.1: Me4NBH(OAc)3 / acetonitrile; acetic acid / 16 h / -30 - 20 °C
6.1: 93 percent / 18 h / 20 °C
7.1: 83 percent / DDQ; 4 Angstroem molecular sieves / CH2Cl2; H2O; various solvent(s) / 0.5 h
8.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 1.75 h / -78 - 0 °C
9.1: LiOH / diethyl ether / 0.25 h / 20 °C
9.2: 85 percent / diethyl ether / 4 h / 20 °C
10.1: 84 percent / aq. HCl / methanol / 6 h / 20 °C
With
hydrogenchloride; lithium hydroxide; boron trifluoride dimethyl etherate; oxalyl dichloride; 4 A molecular sieve; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; acetone; acetonitrile;
1.1: Bayer-Villiger oxidation / 2.1: ortho-Fries rearrangement / 8.1: Swern oxidation / 9.1: Horner-Wadsworth-Emmons reaction / 9.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/1521-3773(20010903)40:17<3186::AID-ANIE3186>3.0.CO;2-W
![(E)-(2R,6S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-6-[(4S,5R,6R)-2,2,5-trimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-[1,3]dioxan-4-yl]-hept-4-en-3-one](/Databaselist/images/loading.webp)
