Technology Process of 6-((10S,13S)-10-Benzyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-13-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid
There total 15 articles about 6-((10S,13S)-10-Benzyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-13-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 2,6-lutidine / CH2Cl2 / 20 °C
2: H2; H(+) / Pd/C / methanol / 20 °C
3: TBTU; N-methylmorpholine; HOBT / dimethylformamide / 20 °C
4: H(+) / CH2Cl2
5: H2; H(+) / Pd/C / methanol / 20 °C
With
4-methyl-morpholine; 2,6-dimethylpyridine; hydrogen; hydrogen cation; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate;
palladium on activated charcoal;
In
methanol; dichloromethane; N,N-dimethyl-formamide;
1: Alkylation / 2: Hydrogenolysis / 3: Cyclization / 4: Alkylation / 5: Hydrogenolysis;
DOI:10.1002/(SICI)1521-3773(19991004)38:19<2902::AID-ANIE2902>3.0.CO;2-2
- Guidance literature:
-
Multi-step reaction with 16 steps
1: 73 percent / tBuLi; trimethylsilylmethyl azide / diethyl ether / -78 °C
2: 92 percent / tetrahydrofuran / 20 °C
3: dimethylformamide / 20 °C
4: TBAF / tetrahydrofuran / 20 °C
5: morpholine / Pd(PPh3)4 / tetrahydrofuran / 20 °C
6: dioxane / Heating
7: 39 percent / H2O; MeOH / penicillin G acyalse / 37 °C
8: NaOH; H2O / dioxane
9: CH2Cl2
10: 91 percent / CF3COOH
11: 90 percent / LiBH4 / tetrahydrofuran / 20 °C
12: 2,6-lutidine / CH2Cl2 / 20 °C
13: H2; H(+) / Pd/C / methanol / 20 °C
14: TBTU; N-methylmorpholine; HOBT / dimethylformamide / 20 °C
15: H(+) / CH2Cl2
16: H2; H(+) / Pd/C / methanol / 20 °C
With
morpholine; 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; sodium hydroxide; lithium borohydride; tetrabutyl ammonium fluoride; water; hydrogen; tert.-butyl lithium; hydrogen cation; trimethylsilylmethyl azide; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; trifluoroacetic acid;
palladium on activated charcoal; tetrakis(triphenylphosphine) palladium(0); penicillin G acyalse;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
1: Substitution / 2: Acylation / 3: Methylation / 4: Alkylation / 5: deallylation / 6: Decarboxylation / 7: Hydrolysis / 8: Acylation / 9: Esterification / 10: Substitution / 11: Reduction / 12: Alkylation / 13: Hydrogenolysis / 14: Cyclization / 15: Alkylation / 16: Hydrogenolysis;
DOI:10.1002/(SICI)1521-3773(19991004)38:19<2902::AID-ANIE2902>3.0.CO;2-2
- Guidance literature:
-
Multi-step reaction with 15 steps
1: 92 percent / tetrahydrofuran / 20 °C
2: dimethylformamide / 20 °C
3: TBAF / tetrahydrofuran / 20 °C
4: morpholine / Pd(PPh3)4 / tetrahydrofuran / 20 °C
5: dioxane / Heating
6: 39 percent / H2O; MeOH / penicillin G acyalse / 37 °C
7: NaOH; H2O / dioxane
8: CH2Cl2
9: 91 percent / CF3COOH
10: 90 percent / LiBH4 / tetrahydrofuran / 20 °C
11: 2,6-lutidine / CH2Cl2 / 20 °C
12: H2; H(+) / Pd/C / methanol / 20 °C
13: TBTU; N-methylmorpholine; HOBT / dimethylformamide / 20 °C
14: H(+) / CH2Cl2
15: H2; H(+) / Pd/C / methanol / 20 °C
With
morpholine; 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; sodium hydroxide; lithium borohydride; tetrabutyl ammonium fluoride; water; hydrogen; hydrogen cation; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; trifluoroacetic acid;
palladium on activated charcoal; tetrakis(triphenylphosphine) palladium(0); penicillin G acyalse;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
1: Acylation / 2: Methylation / 3: Alkylation / 4: deallylation / 5: Decarboxylation / 6: Hydrolysis / 7: Acylation / 8: Esterification / 9: Substitution / 10: Reduction / 11: Alkylation / 12: Hydrogenolysis / 13: Cyclization / 14: Alkylation / 15: Hydrogenolysis;
DOI:10.1002/(SICI)1521-3773(19991004)38:19<2902::AID-ANIE2902>3.0.CO;2-2
