Technology Process of (1R,2S,5S)-2-[(R)-1-(3,5-Dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-2-hydroxy-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid 6-benzyl ester 3-tert-butyl ester
There total 18 articles about (1R,2S,5S)-2-[(R)-1-(3,5-Dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-2-hydroxy-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid 6-benzyl ester 3-tert-butyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(1R,2S,5S)-2-[(R)-1-(3,5-Dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-allyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid 6-benzyl ester 3-tert-butyl ester;
With
ozone;
In
methanol; dichloromethane;
at -78 ℃;
for 0.5h;
With
sodium tetrahydroborate;
In
methanol; dichloromethane;
at 0 ℃;
for 4h;
DOI:10.1021/jo048924i
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 30.4 g / Et3N / CH2Cl2 / 4 h / 25 °C
2.1: 86 percent / Et3Al / NiCl2(dppp) / toluene / 0 - 25 °C
3.1: 72 percent / PhIO; I2 / CH2Cl2 / 24 h / 25 °C
4.1: 97 percent / K2CO3 / methanol; H2O / 4 h / 20 °C
5.1: 97 percent / diphenylphosphoryl azide; PPh3; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C
6.1: SmI2; n-Bu3SnCl / Pd(PPh3)4 / tetrahydrofuran / 12 h / 25 °C
6.2: 120 mg / BF3*OEt2 / CH2Cl2 / 2 h / -40 °C
7.1: SnCl2; thiophenol; Et3N / acetonitrile / 2 h / 0 °C
8.1: 933 mg / Et3N / CH2Cl2 / 3 h / 20 °C
9.1: 81 percent / diisopropyl azodicarboxylate; Ph3P / tetrahydrofuran / 2 h / 20 °C
10.1: O3 / methanol; CH2Cl2 / 0.5 h / -78 °C
10.2: 63 percent / NaBH4 / methanol; CH2Cl2 / 4 h / 0 °C
With
samarium diiodide; di-isopropyl azodicarboxylate; iodosylbenzene; diphenylphosphoranyl azide; tributyltin chloride; iodine; triethylaluminum; potassium carbonate; ozone; thiophenol; triethylamine; triphenylphosphine; tin(ll) chloride;
tetrakis(triphenylphosphine) palladium(0); 1,3-bis[(diphenylphosphino)propane]dichloronickel(II);
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jo048924i
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 25 °C
1.2: 89 percent / tetrahydrofuran; dimethylformamide / 1 h / 25 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C
2.2: 86 percent / tetrahydrofuran; hexane / 0 - 25 °C
3.1: 89 percent / Et3N; 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 3 h / 25 °C
4.1: SmI2; n-Bu3SnCl / Pd(PPh3)4 / tetrahydrofuran / 12 h / 25 °C
4.2: 120 mg / BF3*OEt2 / CH2Cl2 / 2 h / -40 °C
5.1: SnCl2; thiophenol; Et3N / acetonitrile / 2 h / 0 °C
6.1: 933 mg / Et3N / CH2Cl2 / 3 h / 20 °C
7.1: 81 percent / diisopropyl azodicarboxylate; Ph3P / tetrahydrofuran / 2 h / 20 °C
8.1: O3 / methanol; CH2Cl2 / 0.5 h / -78 °C
8.2: 63 percent / NaBH4 / methanol; CH2Cl2 / 4 h / 0 °C
With
dmap; n-butyllithium; samarium diiodide; di-isopropyl azodicarboxylate; tributyltin chloride; sodium hydride; ozone; thiophenol; triethylamine; triphenylphosphine; tin(ll) chloride;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo048924i
![(1R,2S,5S)-2-[(R)-1-(3,5-Dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-allyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid 6-benzyl ester 3-tert-butyl ester](/Databaselist/images/loading.webp)
