Technology Process of (2S,2'S,5'S)-3-(5'-{4''-[N1''',N2'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate
There total 12 articles about (2S,2'S,5'S)-3-(5'-{4''-[N1''',N2'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 98 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.83 h / -60 - 0 °C
2.1: Mg / tetrahydrofuran / 1 h / 20 °C
2.2: 80 percent / tetrahydrofuran / 0.33 h / 20 °C
3.1: Et3N / CH2Cl2 / 1 h / -15 °C
4.1: 11.1 g / aq. HCl / tetrahydrofuran / 4 h / 20 °C
5.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.83 h / -60 - 0 °C
6.1: aq. NaClO2; NaH2PO4*H2O / 2-methyl-propan-2-ol; various solvent(s) / 12 h / 20 °C
7.1: 100 percent / H2 / 10 percent Pd/C / tetrahydrofuran; aq. methanol / 18 h / 20 °C
8.1: 919 mg / BOP; iPr2NEt / acetonitrile / 16 h / 20 °C
9.1: 74 percent / DIAD; PPh3 / tetrahydrofuran / 16 h / 20 °C
With
hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; di-isopropyl azodicarboxylate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; magnesium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; acetonitrile; tert-butyl alcohol;
1.1: Oxidation / 2.1: Metallation / 2.2: Grignard reaction / 3.1: Substitution / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Oxidation / 7.1: Hydrogenolysis / 8.1: Acylation / 9.1: Substitution;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: Mg / tetrahydrofuran / 1 h / 20 °C
1.2: 80 percent / tetrahydrofuran / 0.33 h / 20 °C
2.1: Et3N / CH2Cl2 / 1 h / -15 °C
3.1: 11.1 g / aq. HCl / tetrahydrofuran / 4 h / 20 °C
4.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.83 h / -60 - 0 °C
5.1: aq. NaClO2; NaH2PO4*H2O / 2-methyl-propan-2-ol; various solvent(s) / 12 h / 20 °C
6.1: 100 percent / H2 / 10 percent Pd/C / tetrahydrofuran; aq. methanol / 18 h / 20 °C
7.1: 919 mg / BOP; iPr2NEt / acetonitrile / 16 h / 20 °C
8.1: 74 percent / DIAD; PPh3 / tetrahydrofuran / 16 h / 20 °C
With
hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; di-isopropyl azodicarboxylate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; magnesium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; acetonitrile; tert-butyl alcohol;
1.1: Metallation / 1.2: Grignard reaction / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Oxidation / 6.1: Hydrogenolysis / 7.1: Acylation / 8.1: Substitution;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z