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

Base Information

• Chemical Name: (S)-N¹-allyl-N²-Boc-N¹-(o-nitrobenzenesulfonyl)-5-(triisopropylsilyloxy)pentane-1,2-diamine
• CAS No.: 945492-91-1
• Molecular Formula: C₂₈H₄₉N₃O₇SSi
• Molecular Weight: 599.864
• Mol file: 945492-91-1.mol

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

Chemical Property of (S)-N¹-allyl-N²-Boc-N¹-(o-nitrobenzenesulfonyl)-5-(triisopropylsilyloxy)pentane-1,2-diamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N¹-allyl-N²-Boc-N¹-(o-nitrobenzenesulfonyl)-5-(triisopropylsilyloxy)pentane-1,2-diamine

There total 9 articles about (S)-N¹-allyl-N²-Boc-N¹-(o-nitrobenzenesulfonyl)-5-(triisopropylsilyloxy)pentane-1,2-diamine 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: 61.0%

(S)-2-(N-Boc-amino)-5-(triisopropylsilyloxy)pentan-1-ol (945492-90-0) + N-allyl-o-nitrobenzenesulfonamide (65118-17-4) → (S)-N1-allyl-N2-Boc-N1-(o-nitrobenzenesulfonyl)-5-(triisopropylsilyloxy)pentane-1,2-diamine (945492-91-1)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 20 ℃; for 3h;

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) → (S)-N1-allyl-N2-Boc-N1-(o-nitrobenzenesulfonyl)-5-(triisopropylsilyloxy)pentane-1,2-diamine (945492-91-1)

Guidance literature:

Multi-step reaction with 8 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: 6.46 g / DIBAL-H / tetrahydrofuran; toluene / 1 h / 0 °C

8.1: 61 percent / triphenylphosphine; DIAD / toluene; tetrahydrofuran / 3 h / 20 °C

With sodium tetrahydroborate; di-isopropyl azodicarboxylate; sulfuric acid; hydrogen; potassium carbonate; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene; 8.1: Mitsunobu reaction;

DOI:10.1039/b702649h

Reference yield:

Nα-tert-butyloxycarbonyl-γ-benzyloxycarbonyl-L-glutamic acid methyl ester (59279-58-2) → (S)-N1-allyl-N2-Boc-N1-(o-nitrobenzenesulfonyl)-5-(triisopropylsilyloxy)pentane-1,2-diamine (945492-91-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 42 g / H₂ / Pd/C / ethanol

2.1: triethylamine

3.1: NaBH₄ / methanol; tetrahydrofuran

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

4.2: 6.46 g / DIBAL-H / tetrahydrofuran; toluene / 1 h / 0 °C

5.1: 61 percent / triphenylphosphine; DIAD / toluene; tetrahydrofuran / 3 h / 20 °C

With sodium tetrahydroborate; di-isopropyl azodicarboxylate; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene; 5.1: Mitsunobu reaction;

DOI:10.1039/b702649h

upstream raw materials:

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

N-allyl-o-nitrobenzenesulfonamide

L-glutamic acid

triisopropylsilyl chloride

Downstream raw materials:

C₂₃H₄₁N₃O₅SSi

(2S,5S,6E)-2,5-bis(3-hydroxypropyl)-1-[3-(4-benzyloxyphenyl)propionyl]-7-(2-naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one

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

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