Technology Process of (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester
There total 15 articles about (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 2,6-lutidine / -5 °C
2: 96 percent / (COCl)2; DMSO; Et3N / -78 °C
3: 96 percent / I2; pyridine / CH2Cl2
4: 67 percent / NaBH4; CeCl3*7H2O / methanol
5: 57 percent / DIAD; PPh3 / tetrahydrofuran / 20 °C
6: 72 percent / n-BuLi / tetrahydrofuran / -78 °C
7: 96 percent / NaBH4; CeCl3*7H2O / methanol
8: 78 percent / (PPh3)3RhCl; H2
9: 92 percent / NaH / tetrahydrofuran
10: 90 percent / Na; naphthalene
11: 90 percent / K2CO3
12: aq. KOH / tetrahydrofuran / 0 °C
13: pyBOP; HOBt; DIPEA / CH2Cl2
With
pyridine; 2,6-dimethylpyridine; potassium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; oxalyl dichloride; naphthalene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; sodium; sodium hydride; potassium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane;
2: Swern oxidation / 4: Luche reduction / 5: Mitsunobu reaction / 7: Luche reduction;
DOI:10.1016/j.bmcl.2005.08.062
- Guidance literature:
-
Multi-step reaction with 14 steps
1: K2CO3; MeOH
2: 2,6-lutidine / -5 °C
3: 96 percent / (COCl)2; DMSO; Et3N / -78 °C
4: 96 percent / I2; pyridine / CH2Cl2
5: 67 percent / NaBH4; CeCl3*7H2O / methanol
6: 57 percent / DIAD; PPh3 / tetrahydrofuran / 20 °C
7: 72 percent / n-BuLi / tetrahydrofuran / -78 °C
8: 96 percent / NaBH4; CeCl3*7H2O / methanol
9: 78 percent / (PPh3)3RhCl; H2
10: 92 percent / NaH / tetrahydrofuran
11: 90 percent / Na; naphthalene
12: 90 percent / K2CO3
13: aq. KOH / tetrahydrofuran / 0 °C
14: pyBOP; HOBt; DIPEA / CH2Cl2
With
pyridine; 2,6-dimethylpyridine; methanol; potassium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; oxalyl dichloride; naphthalene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; sodium; sodium hydride; potassium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane;
3: Swern oxidation / 5: Luche reduction / 6: Mitsunobu reaction / 8: Luche reduction;
DOI:10.1016/j.bmcl.2005.08.062
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 96 percent / (COCl)2; DMSO; Et3N / -78 °C
2: 96 percent / I2; pyridine / CH2Cl2
3: 67 percent / NaBH4; CeCl3*7H2O / methanol
4: 57 percent / DIAD; PPh3 / tetrahydrofuran / 20 °C
5: 72 percent / n-BuLi / tetrahydrofuran / -78 °C
6: 96 percent / NaBH4; CeCl3*7H2O / methanol
7: 78 percent / (PPh3)3RhCl; H2
8: 92 percent / NaH / tetrahydrofuran
9: 90 percent / Na; naphthalene
10: 90 percent / K2CO3
11: aq. KOH / tetrahydrofuran / 0 °C
12: pyBOP; HOBt; DIPEA / CH2Cl2
With
pyridine; potassium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; oxalyl dichloride; naphthalene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; sodium; sodium hydride; potassium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane;
1: Swern oxidation / 3: Luche reduction / 4: Mitsunobu reaction / 6: Luche reduction;
DOI:10.1016/j.bmcl.2005.08.062