Technology Process of (2R,4R,6S)-7-(tert-butyldimethylsiloxo)-6-hydroxy-4-[(p-methoxybenzyl)oxy]-2,5,5-trimethylheptyl pivalate
There total 9 articles about (2R,4R,6S)-7-(tert-butyldimethylsiloxo)-6-hydroxy-4-[(p-methoxybenzyl)oxy]-2,5,5-trimethylheptyl pivalate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
1H-imidazole;
In
tetrahydrofuran;
at 25 ℃;
for 3h;
DOI:10.1021/ja993487o
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 96 percent / pyridine / CH2Cl2 / 25 °C
2.1: 81 percent / triflic acid / diethyl ether / 1 h / 20 °C
3.1: 94 percent / TBAF / tetrahydrofuran / 72 h
4.1: 99 percent / DMSO; oxalyl chloride / CH2Cl2 / 1 h / -78 °C
5.1: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 0.33 h / 0 °C
5.2: 89 percent / tetrahydrofuran; toluene / 0.33 h / 0 °C
6.1: 92 percent / osmium tetraoxide; (DHQD)2PYR; potassium ferricyanide / potassium carbonate / H2O; 2-methyl-propan-2-ol / 15 h / 0 °C
7.1: 89 percent / imidazole / tetrahydrofuran / 3 h / 25 °C
With
pyridine; 1H-imidazole; osmium(VIII) oxide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; dimethyl sulfoxide; potassium hexacyanoferrate(III);
potassium carbonate;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol;
1.1: Esterification / 2.1: benzylation / 3.1: desilylation / 4.1: Swern oxidation / 5.1: Metallation / 5.2: Wittig olefination / 6.1: hydroxylation / 7.1: silylation;
DOI:10.1021/ja993487o
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 93 percent / LiBH4 / diethyl ether; methanol / 0.5 h / 0 °C
2.1: 96 percent / pyridine / CH2Cl2 / 25 °C
3.1: 81 percent / triflic acid / diethyl ether / 1 h / 20 °C
4.1: 94 percent / TBAF / tetrahydrofuran / 72 h
5.1: 99 percent / DMSO; oxalyl chloride / CH2Cl2 / 1 h / -78 °C
6.1: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 0.33 h / 0 °C
6.2: 89 percent / tetrahydrofuran; toluene / 0.33 h / 0 °C
7.1: 92 percent / osmium tetraoxide; (DHQD)2PYR; potassium ferricyanide / potassium carbonate / H2O; 2-methyl-propan-2-ol / 15 h / 0 °C
8.1: 89 percent / imidazole / tetrahydrofuran / 3 h / 25 °C
With
pyridine; 1H-imidazole; osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; dimethyl sulfoxide; potassium hexacyanoferrate(III);
potassium carbonate;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol;
1.1: Ring cleavage / 2.1: Esterification / 3.1: benzylation / 4.1: desilylation / 5.1: Swern oxidation / 6.1: Metallation / 6.2: Wittig olefination / 7.1: hydroxylation / 8.1: silylation;
DOI:10.1021/ja993487o
