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

Base Information

• Chemical Name: 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
• CAS No.: 144610-87-7
• Molecular Formula: C₃₉H₅₉N₃O₉Si
• Molecular Weight: 741.998
• Mol file: 144610-87-7.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 13 articles about 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 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: 91.0%

N-benzyloxycarbonyl-L-isoleucine (3160-59-6,4276-05-5,28862-89-7,55723-45-0,55723-48-3,127866-12-0) + methyl (2S,3S)-3-<4-<2-amino-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>prolinate (144610-85-5,144610-86-6) → 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 (144610-87-7,144666-21-7)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 3h;

DOI:10.1021/ja00052a015

Reference yield:

(2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinal (144610-81-1) → 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 (144610-87-7,144666-21-7)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/ja00052a015

Reference yield:

(2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>proline (144610-82-2) → 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 (144610-87-7,144666-21-7)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/ja00052a015

upstream raw materials:

N-benzyloxycarbonyl-L-isoleucine

methyl (2S,3S)-3-<4-<2-amino-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>prolinate

4-cyanophenol

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

Downstream raw materials:

(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

pentafluorophenyl (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

Refernces

• 1、 Heffner,Joullie. "Studies directed toward the total synthesis of 14-membered cyclopeptide alkaloids: Synthesis of a cyclic precursor to nummularine-F". . p. 7021 - 7024. Retrieved 2007/10/02.