Technology Process of (E)-(2S,3R,4R,5S)-4-Benzyloxy-2-tert-butoxycarbonylamino-3,5-dihydroxy-icos-6-enoic acid
There total 14 articles about (E)-(2S,3R,4R,5S)-4-Benzyloxy-2-tert-butoxycarbonylamino-3,5-dihydroxy-icos-6-enoic acid 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:
-
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
Yield given;
DOI:10.1021/ja9730829
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 1.) BuLi, 2.) HMPA / 1.) THF, 2.) THF, from -78 deg C to RT
2: 96 percent / 3 N aq. HCl / tetrahydrofuran / Ambient temperature
3: Et3N, DMAP / CH2Cl2 / 0 °C
4: LiAlH4 / tetrahydrofuran / Heating
5: imidazole / dimethylformamide
6: 83 percent / HCOOH / diethyl ether
7: 95 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -50 °C
8: 1.) LDA, 2.) ZnCl2
9: CH2Cl2
10: aq. LiOH / tetrahydrofuran / 0 h
11: TBAF / tetrahydrofuran
With
1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; zinc(II) chloride; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja9730829
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 1.) BuLi, 2.) HMPA / 1.) THF, 2.) THF, from -78 deg C to RT
2: 96 percent / 3 N aq. HCl / tetrahydrofuran / Ambient temperature
3: Et3N, DMAP / CH2Cl2 / 0 °C
4: LiAlH4 / tetrahydrofuran / Heating
5: imidazole / dimethylformamide
6: 83 percent / HCOOH / diethyl ether
7: 95 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -50 °C
8: 1.) LDA, 2.) ZnCl2
9: CH2Cl2
10: aq. LiOH / tetrahydrofuran / 0 h
11: TBAF / tetrahydrofuran
With
1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; zinc(II) chloride; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja9730829
