Technology Process of (2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester
There total 17 articles about (2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
Multi-step reaction with 16 steps
1: 2) ethyl acetate, reflux
2: LiBH4 / diethyl ether
3: Zn(N3)2(py)2, Ph3P, DEAD, imid / toluene
4: H2 / 10percent Pd/C / ethanol
5: pyridine / CH2Cl2
6: TBAF / tetrahydrofuran / 0 to 25 deg C
7: (COCl)2, DMSO, DIPEA / CH2Cl2
8: BF3*Et2O / CH2Cl2 / -78 - -20 °C
9: DIPEA / CH2Cl2 / 0 °C
10: OsO4, NMO / acetone; butan-1-ol; H2O
11: NaIO4 / tetrahydrofuran; H2O
12: toluene / 70 °C
13: 85 percent / 8.8 eq. NaBH4 / methanol
14: DIPEA / CH2Cl2
15: LiBH4 / tetrahydrofuran / Heating
16: (COCl)2, DMSO, DIPEA / CH2Cl2
With
pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; oxalyl dichloride; Zn(N3)2/bis-pyridine complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; butan-1-ol;
DOI:10.1021/jo00062a003
- Guidance literature:
-
Multi-step reaction with 14 steps
1: Zn(N3)2(py)2, Ph3P, DEAD, imid / toluene
2: H2 / 10percent Pd/C / ethanol
3: pyridine / CH2Cl2
4: TBAF / tetrahydrofuran / 0 to 25 deg C
5: (COCl)2, DMSO, DIPEA / CH2Cl2
6: BF3*Et2O / CH2Cl2 / -78 - -20 °C
7: DIPEA / CH2Cl2 / 0 °C
8: OsO4, NMO / acetone; butan-1-ol; H2O
9: NaIO4 / tetrahydrofuran; H2O
10: toluene / 70 °C
11: 85 percent / 8.8 eq. NaBH4 / methanol
12: DIPEA / CH2Cl2
13: LiBH4 / tetrahydrofuran / Heating
14: (COCl)2, DMSO, DIPEA / CH2Cl2
With
pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; oxalyl dichloride; Zn(N3)2/bis-pyridine complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; butan-1-ol;
DOI:10.1021/jo00062a003
- Guidance literature:
-
Multi-step reaction with 13 steps
1: H2 / 10percent Pd/C / ethanol
2: pyridine / CH2Cl2
3: TBAF / tetrahydrofuran / 0 to 25 deg C
4: (COCl)2, DMSO, DIPEA / CH2Cl2
5: BF3*Et2O / CH2Cl2 / -78 - -20 °C
6: DIPEA / CH2Cl2 / 0 °C
7: OsO4, NMO / acetone; butan-1-ol; H2O
8: NaIO4 / tetrahydrofuran; H2O
9: toluene / 70 °C
10: 85 percent / 8.8 eq. NaBH4 / methanol
11: DIPEA / CH2Cl2
12: LiBH4 / tetrahydrofuran / Heating
13: (COCl)2, DMSO, DIPEA / CH2Cl2
With
pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; butan-1-ol;
DOI:10.1021/jo00062a003