Technology Process of (3S,5R)-2,5-Dimethyl-6-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hexan-3-ol
There total 1 articles about (3S,5R)-2,5-Dimethyl-6-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hexan-3-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 11 steps
1.1: 42.55 g / imidazole / dimethylformamide / 24 h
2.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C
2.2: hexane; tetrahydrofuran / 1 h / -78 °C
3.1: 13.85 g / aq. HF / acetonitrile / 20 °C
4.1: H2 / Pd/C / methanol / 12 h / 20 °C / 760 Torr
5.1: 3.69 g / LiAlH4 / tetrahydrofuran / 1 h / 0 °C
6.1: pyridine / CH2Cl2 / 0 °C
7.1: aq. K2CO3 / methanol / 5 h
8.1: 3.64 mg / Dess-Martin reagent / CH2Cl2 / 3 h / 0 °C
9.1: CF3SO3H; Et3B; DIPEA / hexane; CH2Cl2 / 0.5 h / -10 °C
9.2: 88 percent / TiCl4 / hexane; CH2Cl2 / 2 h
10.1: LiAlH4 / tetrahydrofuran / 0.5 h / Heating
11.1: PPTs / 24 h
With
pyridine; 1H-imidazole; lithium aluminium tetrahydride; triethyl borane; trifluorormethanesulfonic acid; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
2.2: Peterson reaction / 8.1: Dess-Martin oxidation;
DOI:10.1002/chem.200600599
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(E)-(2S,3S,5S,7S,10S,16S,19S,22S,27S)-16-((S)-sec-Butyl)-3-hydroxy-7-isopropyl-22-(4-methoxy-benzyl)-2,5,17,19,20,25-hexamethyl-8,29-dioxa-14,17,20,23,30-pentaaza-tricyclo[25.2.1.010,14]triaconta-1(30),25-diene-9,15,18,21,24-pentaone
- Guidance literature:
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Multi-step reaction with 10 steps
1: 82 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene
2: TsOH / methanol
3: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO3 / NaClO / CH2Cl2; H2O / 1 h
4: NaClO2; NaH2PO4 / H2O; 2-methyl-propan-2-ol; various solvent(s) / 1 h
5: HATU; DIPEA / CH2Cl2 / 24 h
6: 69 percent / (diethylamino)sulfur trifluoride / CH2Cl2 / 3 h / -78 °C
7: N-methylaniline / [Pd(PPh3)4] / tetrahydrofuran / 2 h
8: HATU; DIPEA / CH2Cl2 / 48 h / 20 °C
9: tetrabutylammonium fluoride / tetrahydrofuran
10: HATU; DIPEA / CH2Cl2
With
dmap; sodium chlorite; sodium dihydrogenphosphate; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; diethylamino-sulfur trifluoride; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-methylaniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide;
sodium hypochlorite; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1002/chem.200600599
- Guidance literature:
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Multi-step reaction with 9 steps
1: 82 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene
2: TsOH / methanol
3: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO3 / NaClO / CH2Cl2; H2O / 1 h
4: NaClO2; NaH2PO4 / H2O; 2-methyl-propan-2-ol; various solvent(s) / 1 h
5: HATU; DIPEA / CH2Cl2 / 24 h
6: 69 percent / (diethylamino)sulfur trifluoride / CH2Cl2 / 3 h / -78 °C
7: N-methylaniline / [Pd(PPh3)4] / tetrahydrofuran / 2 h
8: HATU; DIPEA / CH2Cl2 / 48 h / 20 °C
9: tetrabutylammonium fluoride / tetrahydrofuran
With
dmap; sodium chlorite; sodium dihydrogenphosphate; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; diethylamino-sulfur trifluoride; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-methylaniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide;
sodium hypochlorite; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1002/chem.200600599