(2R,S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide

Base Information

• Chemical Name: (2R,S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide
• CAS No.: 945492-94-4
• Molecular Formula: C₅₆H₈₈N₄O₉SSi₂
• Molecular Weight: 1049.57
• Mol file: 945492-94-4.mol

Synonyms:(2R,S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide

Chemical Property of (2R,S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide

There total 25 articles about (2R,S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide 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:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid (35793-73-8) → (2R,S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide (945492-94-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate / dimethylformamide

2.1: 35 g / H₂ / Pd/C / ethanol

3.1: triethylamine

4.1: NaBH₄ / methanol; tetrahydrofuran

5.1: triethylamine / dimethylformamide / 5 h / 20 °C

5.2: 7.00 g / DIBAL-H / tetrahydrofuran; toluene / 1 h / 0 °C

6.1: 66 percent / triphenylphosphine; DIAD / toluene; tetrahydrofuran / 3 h / 20 °C

7.1: TFA / CH₂Cl₂ / 0 °C

8.1: 2.72 g / 1-hydroxy-7-azabenzotriazole; HATU; DIEA / dimethylformamide / 20 °C

With sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; di-isopropyl azodicarboxylate; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 6.1: Mitsunobu reaction;

DOI:10.1039/b702649h

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (2R,S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide (945492-94-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: H₂SO₄

1.2: pyridine / ethanol

2.1: triethylamine / dimethylformamide

3.1: potassium carbonate / dimethylformamide

4.1: 42 g / H₂ / Pd/C / ethanol

5.1: triethylamine

6.1: NaBH₄ / methanol; tetrahydrofuran

7.1: triethylamine / dimethylformamide / 5 h / 20 °C

7.2: TFA / CH₂Cl₂ / 1 h / 0 °C

8.1: 4.95 g / triethylamine / CH₂Cl₂

9.1: 82 percent / potassium carbonate / dimethylformamide / 3 h / 20 °C

10.1: 90 percent / mercaptoacetic acid; LiOH*H₂O / dimethylformamide / 1 h / 20 °C

11.1: 95 percent / HATU; triethylamine / dimethylformamide / 3 h / 20 °C

12.1: 88 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 3 h / 0 °C

13.1: 2.72 g / 1-hydroxy-7-azabenzotriazole; HATU; DIEA / dimethylformamide / 20 °C

With lithium hydroxide; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; sulfuric acid; hydrogen; potassium carbonate; mercaptoacetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/b702649h

Reference yield:

L-glutamic acid γ-benzyl ester (1676-73-9,25014-27-1) → (2R,S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide (945492-94-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: triethylamine / dimethylformamide

2.1: potassium carbonate / dimethylformamide

3.1: 42 g / H₂ / Pd/C / ethanol

4.1: triethylamine

5.1: NaBH₄ / methanol; tetrahydrofuran

6.1: triethylamine / dimethylformamide / 5 h / 20 °C

6.2: TFA / CH₂Cl₂ / 1 h / 0 °C

7.1: 4.95 g / triethylamine / CH₂Cl₂

8.1: 82 percent / potassium carbonate / dimethylformamide / 3 h / 20 °C

9.1: 90 percent / mercaptoacetic acid; LiOH*H₂O / dimethylformamide / 1 h / 20 °C

10.1: 95 percent / HATU; triethylamine / dimethylformamide / 3 h / 20 °C

11.1: 88 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 3 h / 0 °C

12.1: 2.72 g / 1-hydroxy-7-azabenzotriazole; HATU; DIEA / dimethylformamide / 20 °C

With lithium hydroxide; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; hydrogen; potassium carbonate; mercaptoacetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/b702649h

upstream raw materials:

C₂₃H₄₁N₃O₅SSi

(S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-5-(triisopropylsilyloxy)pentanoic acid

(R)-2-(N-Boc-amino)-5-(triisopropylsilyloxy)pentan-1-ol

(R)-N¹-allyl-N²-Boc-N¹-(o-nitrobenzenesulfonyl)-5-(triisopropylsilyloxy)pentane-1,2-diamine

Downstream raw materials:

(2R,5R,6E)-2,5-bis[3-(triisopropylsilyloxy)propyl]-1-[3-(4-benzyloxyphenyl)propionyl]-7-(o-nitrobenzenesulfonyl)-1,4,7-triazacycloundec-9-en-3-one

(2S,5R,6E)-2,5-bis[3-(triisopropylsilyloxy)propyl]-1-[3-(4-benzyloxyphenyl)propionyl]-7-(o-nitrobenzenesulfonyl)-1,4,7-triazacycloundec-9-en-3-one

Triphenylphosphine oxide