(2S,3S)-3-<4-<2-(N-(N-carbobenzoxy-(S)-isoleucyl)amino)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>proline

Base Information

Chemical Name:(2S,3S)-3-<4-<2-(N-(N-carbobenzoxy-(S)-isoleucyl)amino)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>proline
CAS No.:144610-88-8
Molecular Formula:C₃₈H₅₇N₃O₉Si
Molecular Weight:727.971
Hs Code.:

(2S,3S)-3-<4-<2-(N-(N-carbobenzoxy-(S)-isoleucyl)amino)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>proline

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Chemical Property of (2S,3S)-3-<4-<2-(N-(N-carbobenzoxy-(S)-isoleucyl)amino)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>proline

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Technology Process of (2S,3S)-3-<4-<2-(N-(N-carbobenzoxy-(S)-isoleucyl)amino)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>proline

There total 14 articles about (2S,3S)-3-<4-<2-(N-(N-carbobenzoxy-(S)-isoleucyl)amino)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>proline 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:

Reference yield: 90.0%

: 144610-87-7,144666-21-7
methyl (2S,3S)-3-<4-<2-(N-(N-carbobenzoxy-(S)-isoleucyl)amino)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>prolinate

: 144610-88-8,144666-22-8
(2S,3S)-3-<4-<2-(N-(N-carbobenzoxy-(S)-isoleucyl)amino)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>proline

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; at 5 ℃; for 3h;
DOI:10.1021/ja00052a015

Reference yield:

: 144610-81-1
(2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinal

: 144610-88-8,144666-22-8
(2S,3S)-3-<4-<2-(N-(N-carbobenzoxy-(S)-isoleucyl)amino)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>proline

Guidance literature:: Multi-step reaction with 8 steps

1: 93.5 percent / 1.25 M NaHPO₄*H₂O buffer, 1 M aq. KMnO₄ / 2-methyl-propan-2-ol; CH₂Cl₂

2: 81 percent / 4-(N,N-dimethylamino)pyridine, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 3 h

3: 78 percent / NaH₂PO₂, Raney nickel / pyridine; acetic acid; H₂O / 2 h / 40 °C

4: NaOMe / methanol / 7 h / 25 °C

5: 72 percent / imidazole / dimethylformamide / 24 h / 25 °C

6: 91 percent / ammonium formate / 10percent Pd/C / methanol / 4 h / 25 °C

7: 91 percent / 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole hydrate (HOBT), N-methylmorpholine (NMM) / CH₂Cl₂ / 3 h / 25 °C

8: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 5 °C

With 4-methyl-morpholine; 1H-imidazole; dmap; lithium hydroxide; potassium permanganate; sodium hypophosphite; NaHPO₄*H₂O buffer; sodium methylate; ammonium formate; nickel; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja00052a015

Reference yield:

: 144610-82-2
(2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>proline

: 144610-88-8,144666-22-8
(2S,3S)-3-<4-<2-(N-(N-carbobenzoxy-(S)-isoleucyl)amino)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>proline

Guidance literature:: Multi-step reaction with 7 steps

1: 81 percent / 4-(N,N-dimethylamino)pyridine, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 3 h

2: 78 percent / NaH₂PO₂, Raney nickel / pyridine; acetic acid; H₂O / 2 h / 40 °C

3: NaOMe / methanol / 7 h / 25 °C

4: 72 percent / imidazole / dimethylformamide / 24 h / 25 °C

5: 91 percent / ammonium formate / 10percent Pd/C / methanol / 4 h / 25 °C

6: 91 percent / 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole hydrate (HOBT), N-methylmorpholine (NMM) / CH₂Cl₂ / 3 h / 25 °C

7: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 5 °C

With 4-methyl-morpholine; 1H-imidazole; dmap; lithium hydroxide; sodium hypophosphite; sodium methylate; ammonium formate; nickel; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/ja00052a015