Technology Process of (7R,11R,14R,17S,20S,E)-20-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-7-hydroxy-11,14-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-17-tritylthiomethyl-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oic acid
There total 14 articles about (7R,11R,14R,17S,20S,E)-20-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-7-hydroxy-11,14-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-17-tritylthiomethyl-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oic 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:
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620567-97-7
methyl (7R,11R,14R,17S,20S,E)-20-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-7-hydroxy-11,14-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-17-tritylthiomethyl-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oate
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620567-24-0
(7R,11R,14R,17S,20S,E)-20-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-7-hydroxy-11,14-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-17-tritylthiomethyl-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oic acid
- Guidance literature:
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With
lithium hydroxide monohydrate;
In
tetrahydrofuran; water;
at 0 ℃;
for 9h;
DOI:10.1002/ejoc.201601023
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620567-24-0
(7R,11R,14R,17S,20S,E)-20-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-7-hydroxy-11,14-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-17-tritylthiomethyl-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oic acid
- Guidance literature:
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Multi-step reaction with 8 steps
1: 3.36 g / imidazole / 27 / 2 h / 20 °C
2: Et2NH / CH2Cl2 / 3 h / 0 °C
3: 3.65 g / EDC; HOBt / dimethylformamide; CH2Cl2 / 20 h / 20 °C
4: Et2NH / CH2Cl2 / 4 h / 0 °C
5: 3.20 g / EDC; HOBt / dimethylformamide; CH2Cl2 / 20 h / 20 °C
6: 100 percent / Et2NH / CH2Cl2 / 6 h / 0 - 20 °C
7: 100 percent / BOP; DIPEA / CH2Cl2; acetonitrile / 1 h / 20 °C
8: 79 percent / aq. LiOH / tetrahydrofuran / 20 °C
With
1H-imidazole; lithium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; N-ethyl-N,N-diisopropylamine;
27;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo034765b
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620567-24-0
(7R,11R,14R,17S,20S,E)-20-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-7-hydroxy-11,14-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-17-tritylthiomethyl-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oic acid
- Guidance literature:
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Multi-step reaction with 7 steps
1.1: Et3N / CH2Cl2 / 1 h / 20 °C
2.1: 1.06 g / benzene / 7 h / Heating
3.1: (n-Bu)2BOTf; DIPEA / CH2Cl2 / 1 h / 20 °C
3.2: 69 percent / CH2Cl2 / 8 h / -78 - -10 °C
4.1: 100 percent / Al-Hg / tetrahydrofuran; H2O / 2 h / 0 °C
5.1: 78 percent / aq. LiOH; aq. H2O2 / tetrahydrofuran / 1 h / 0 °C
6.1: 100 percent / BOP; DIPEA / CH2Cl2; acetonitrile / 1 h / 20 °C
7.1: 79 percent / aq. LiOH / tetrahydrofuran / 20 °C
With
lithium hydroxide; aluminium amalgam; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; dichloromethane; water; acetonitrile; benzene;
DOI:10.1021/jo034765b