Technology Process of [26-azido-6-{2-[3-(2-benzyloxycarbonylamino-acetylamino)-4-hydroxy-phenyl]-ethyl}-11-hydroxy-3,15-bis-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.09,13]heptacos-18-yl]-carbamic acid tert-butyl ester
There total 25 articles about [26-azido-6-{2-[3-(2-benzyloxycarbonylamino-acetylamino)-4-hydroxy-phenyl]-ethyl}-11-hydroxy-3,15-bis-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.09,13]heptacos-18-yl]-carbamic acid tert-butyl ester 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:
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551929-86-3
[26-azido-6-{2-[3-(2-benzyloxycarbonylamino-acetylamino)-4-hydroxy-phenyl]-ethyl}-11-hydroxy-3,15-bis-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.09,13]heptacos-18-yl]-carbamic acid tert-butyl ester
- Guidance literature:
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Multi-step reaction with 13 steps
1: 88 percent / AlCl3
2: 90 percent / H2 / Pd/C
3: HBr; AcOH
4: NaNO2; AcOH
5: H2 / Pd/C
6: tetrahydrofuran
7: EDC; HOBT
8: DIEA / acetonitrile
9: CMC; HOBT
10: DIEA / acetonitrile
11: aq. LiOH / tetrahydrofuran
12: DPPA; NaHCO3 / dimethylformamide
With
lithium hydroxide; aluminium trichloride; diphenyl-phosphinic acid; hydrogen bromide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;
1: Friedel-Craft's reaction;
DOI:10.1016/S0960-894X(02)00978-2
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551929-86-3
[26-azido-6-{2-[3-(2-benzyloxycarbonylamino-acetylamino)-4-hydroxy-phenyl]-ethyl}-11-hydroxy-3,15-bis-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.09,13]heptacos-18-yl]-carbamic acid tert-butyl ester
- Guidance literature:
-
Multi-step reaction with 10 steps
1: NaNO2; AcOH
2: H2 / Pd/C
3: tetrahydrofuran
4: EDC; HOBT
5: DIEA / acetonitrile
6: CMC; HOBT
7: DIEA / acetonitrile
8: aq. LiOH / tetrahydrofuran
9: DPPA; NaHCO3 / dimethylformamide
With
lithium hydroxide; diphenyl-phosphinic acid; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0960-894X(02)00978-2
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-
551929-86-3
[26-azido-6-{2-[3-(2-benzyloxycarbonylamino-acetylamino)-4-hydroxy-phenyl]-ethyl}-11-hydroxy-3,15-bis-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.09,13]heptacos-18-yl]-carbamic acid tert-butyl ester
- Guidance literature:
-
Multi-step reaction with 9 steps
1: NaNO2; AcOH
2: H2 / Pd/C
3: tetrahydrofuran
4: EDC; HOBT
5: DIEA / acetonitrile
6: CMC; HOBT
7: DIEA / acetonitrile
8: aq. LiOH / tetrahydrofuran
9: DPPA; NaHCO3 / dimethylformamide
With
lithium hydroxide; diphenyl-phosphinic acid; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0960-894X(02)00978-2