4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester

Base Information

• Chemical Name: 4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester
• CAS No.: 345664-76-8
• Molecular Formula: C₅₃H₉₁N₅O₁₃Si
• Molecular Weight: 1034.42
• Mol file: 345664-76-8.mol

Synonyms:4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester

Chemical Property of 4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester

There total 19 articles about 4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl 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:

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → 4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester (345664-76-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.204 g / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

2: NaOH / tetrahydrofuran; methanol; H₂O / 0 - 20 °C

3: 0.5774 g / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / toluene / 0 - 20 °C

4: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

5: 0.2315 g / EDAC*HCl; 4-dimethylaminopyridine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

6: 96 percent / ethyldiisopropylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

7: magnesium bromide diethyl etherate / CH₂Cl₂ / 6 h / 0 - 20 °C

8: H₂ / Pd/C / methanol; ethyl acetate / 5 h / 20 °C

With morpholine; 2,6-dimethylpyridine; dmap; sodium hydroxide; hydrogen; magnesium bromide ethyl etherate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/ol9910058

Reference yield:

C61H97N5O15Si (345664-75-7) → 4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester (345664-76-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; at 20 ℃;

DOI:10.1021/ja010222c

Reference yield:

L-2-hydroxy-3-methylbutanoic acid allyl ester (178113-56-9) → 4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester (345664-76-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 0.5774 g / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / toluene / 0 - 20 °C

2: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

3: 0.2315 g / EDAC*HCl; 4-dimethylaminopyridine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

4: 96 percent / ethyldiisopropylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

5: magnesium bromide diethyl etherate / CH₂Cl₂ / 6 h / 0 - 20 °C

6: H₂ / Pd/C / methanol; ethyl acetate / 5 h / 20 °C

With morpholine; dmap; hydrogen; magnesium bromide ethyl etherate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ol9910058

upstream raw materials:

C₆₁H₉₇N₅O₁₅Si

(S)-2-Hydroxy-3-methylbutanoic acid

triisopropylsilyl trifluoromethanesulfonate

Z-leucylprolyl-N,O-dimethyltyrosine-O-Boc-threonine-OSEM

Downstream raw materials:

C₅₃H₈₉N₅SiO₁₂

(-)-tamandarin A

N-Z-prolyl-[Hiv²] didemnin A

(5S,8S,12S,13R,16S,17R,20S,22aS)-16-Amino-13-((S)-sec-butyl)-12-hydroxy-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-tetradecahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacyclohenicosene-4,7,10,15,19,22-hexaone

Refernces

• 1、 Liang,Portonovo,Vera,Xiao,Joullie. "The first total synthesis of (-)-tamandarin A.". . p. 1319 - 1322. Retrieved 2008/02/09.