3(S)-(N^α-benzoyl-glycyl-prolyl-leucyl-amino)-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol

Base Information

• Chemical Name: 3(S)-(N^α-benzoyl-glycyl-prolyl-leucyl-amino)-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol
• CAS No.: 386750-00-1
• Molecular Formula: C₃₅H₅₉N₅O₇Si
• Molecular Weight: 689.968

Synonyms:3(S)-(N^α-benzoyl-glycyl-prolyl-leucyl-amino)-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol

Chemical Property of 3(S)-(N^α-benzoyl-glycyl-prolyl-leucyl-amino)-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol

Chemical Property:

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Technology Process of 3(S)-(N^α-benzoyl-glycyl-prolyl-leucyl-amino)-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol

There total 1 articles about 3(S)-(N^α-benzoyl-glycyl-prolyl-leucyl-amino)-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol 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: 69.0%

3(S)-amino-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol (386749-97-9) + Bz-Gly-Pro-Leu-OH → 3(S)-(Nα-benzoyl-glycyl-prolyl-leucyl-amino)-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol (386750-00-1)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at -3 - 0 ℃;

DOI:10.1248/cpb.49.1272

Reference yield: 95.0%

3(S)-(Nα-benzoyl-glycyl-prolyl-leucyl-amino)-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol (386750-00-1) → [(1S,2S)-2-((S)-2-{[(S)-1-(2-Benzoylamino-acetyl)-pyrrolidine-2-carbonyl]-amino}-4-methyl-pentanoylamino)-1-hydroxymethyl-propyl]-carbamic acid tert-butyl ester (685831-16-7)

Guidance literature:

With acetic acid; at 20 ℃; for 4h;

DOI:10.1248/cpb.49.1272

Reference yield:

3(S)-(Nα-benzoyl-glycyl-prolyl-leucyl-amino)-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol (386750-00-1) → (2S,3S)-3-((S)-2-{[(S)-1-(2-Benzoylamino-acetyl)-pyrrolidine-2-carbonyl]-amino}-4-methyl-pentanoylamino)-2-tert-butoxycarbonylamino-butyric acid

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / 70 percent aq. AcOH / 4 h / 20 °C

2: 62 percent / pyridinium dichromate / dimethylformamide / 16 h / 20 °C

With dipyridinium dichromate; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.49.1272

upstream raw materials:

3(S)-amino-2(R)-(tert-butyloxycarbonylamino)-O-tert-butyldimethylsilylbutanol

Downstream raw materials:

[(1S,2S)-2-((S)-2-{[(S)-1-(2-Benzoylamino-acetyl)-pyrrolidine-2-carbonyl]-amino}-4-methyl-pentanoylamino)-1-hydroxymethyl-propyl]-carbamic acid tert-butyl ester

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