Technology Process of 1-[(2S,3R,8R,9S)-3-(tert-butyldimethyl-silanyloxy)-9-ethyl-8-benzyloxy-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-3-methylbutane-2,3-diol
There total 12 articles about 1-[(2S,3R,8R,9S)-3-(tert-butyldimethyl-silanyloxy)-9-ethyl-8-benzyloxy-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-3-methylbutane-2,3-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
perchloric acid;
In
tetrahydrofuran;
for 8h;
DOI:10.1021/ja029956v
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 90 percent / CuI / tetrahydrofuran; diethyl ether / 1 h / -20 °C
2.1: NaH / tetrahydrofuran / 0 - 25 °C
2.2: 90 percent / tetrahydrofuran / 10 h / 25 °C
3.1: Et3N / diethyl ether / -78 - 0 °C
4.1: n-BuLi / tetrahydrofuran; hexane
4.2: 28.6 g / tetrahydrofuran; hexane / -78 - 0 °C
5.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -78 °C
5.2: 82 percent / tetrahydrofuran / 1.5 h / -40 °C
6.1: 82 percent / NaBH4 / tetrahydrofuran; H2O / 14 h / 25 °C
7.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -15 °C
8.1: methoxyborane derived from 2-carene / diethyl ether / 1 h
8.2: diethyl ether / 2 h
8.3: aq. NaOH; aq. H2O2 / tetrahydrofuran / 3 h / Heating
9.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1.5 h
10.1: 80 percent / meta-chloroperoxybenzoic acid / CH2Cl2 / -40 - 25 °C
11.1: 80 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 14 h
12.1: 65 percent / aq. HClO4 / tetrahydrofuran / 8 h
With
2,6-dimethylpyridine; sodium tetrahydroborate; copper(l) iodide; Grubbs catalyst first generation; n-butyllithium; perchloric acid; oxalyl dichloride; methoxyborane derived from 2-carene; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;
7.1: Swern oxidation;
DOI:10.1021/ja029956v
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: NaH / tetrahydrofuran / 0 - 25 °C
1.2: 90 percent / tetrahydrofuran / 10 h / 25 °C
2.1: Et3N / diethyl ether / -78 - 0 °C
3.1: n-BuLi / tetrahydrofuran; hexane
3.2: 28.6 g / tetrahydrofuran; hexane / -78 - 0 °C
4.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -78 °C
4.2: 82 percent / tetrahydrofuran / 1.5 h / -40 °C
5.1: 82 percent / NaBH4 / tetrahydrofuran; H2O / 14 h / 25 °C
6.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -15 °C
7.1: methoxyborane derived from 2-carene / diethyl ether / 1 h
7.2: diethyl ether / 2 h
7.3: aq. NaOH; aq. H2O2 / tetrahydrofuran / 3 h / Heating
8.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1.5 h
9.1: 80 percent / meta-chloroperoxybenzoic acid / CH2Cl2 / -40 - 25 °C
10.1: 80 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 14 h
11.1: 65 percent / aq. HClO4 / tetrahydrofuran / 8 h
With
2,6-dimethylpyridine; sodium tetrahydroborate; Grubbs catalyst first generation; n-butyllithium; perchloric acid; oxalyl dichloride; methoxyborane derived from 2-carene; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;
6.1: Swern oxidation;
DOI:10.1021/ja029956v
![[(2S,3R,8R,9S)-8-benzyloxy-2-(3,3-dimethyl-oxiranylmethyl)-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy]-tert-butyl-dimethyl-silane](/Databaselist/images/loading.webp)
