(S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester
• CAS No.: 864239-09-8
• Molecular Formula: C₅₅H₆₆N₄O₈
• Molecular Weight: 911.151
• Mol file: 864239-09-8.mol

Synonyms:(S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester

Chemical Property of (S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester

There total 9 articles about (S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl 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:

(S)-2-((2R,4S,5S)-5-Amino-4-benzyloxy-2,7-dimethyl-octanoylamino)-propionic acid benzyl ester + Nα-tert-butoxycarbonyl-Nω-triphenylmethyl-L-asparagine (132388-68-2) → (S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester (864239-09-8)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 14h;

DOI:10.1021/jm050142+

Reference yield:

((1S,2S,4R)-2-Benzyloxy-1-isobutyl-4-methyl-5-oxo-pentyl)-carbamic acid tert-butyl ester → (S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester (864239-09-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 38.3 mg / aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / acetonitrile; 2-methyl-propan-2-ol / 0.5 h / 0 °C

2: 77 percent / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 14 h / 5 °C

3: HCl / dioxane / 0.33 h

4: 65 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 14 h / 0 - 20 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jm050142+

Reference yield:

2,2-dimethylpropionic acid (5S)-tert-butoxycarbonylamino-(4S)-hydroxy-(2R),7-dimethyloctyl ester (864239-05-4) → (S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester (864239-09-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 69 percent / n-Bu₄NI; NaH / tetrahydrofuran / 14 h / 20 °C

2: DibalH / CH₂Cl₂; toluene / 0.5 h / -78 °C

3: Et₃N; SO₃*Py / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

4: 38.3 mg / aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / acetonitrile; 2-methyl-propan-2-ol / 0.5 h / 0 °C

5: 77 percent / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 14 h / 5 °C

6: HCl / dioxane / 0.33 h

7: 65 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 14 h / 0 - 20 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridine-SO₃ complex; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jm050142+

upstream raw materials:

N^α-tert-butoxycarbonyl-N^ω-triphenylmethyl-L-asparagine

2,2-dimethylpropionic acid (5S)-tert-butoxycarbonylamino-(4S)-hydroxy-(2R),7-dimethyloctyl ester

(4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctanoic acid

2,2-dimethylpropionic acid (4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctyl ester

Downstream raw materials:

(S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester

(S)-4-{(S)-1-[(S)-1-[(1S,2S,4R)-2-Benzyloxy-4-((S)-1-benzyloxycarbonyl-ethylcarbamoyl)-1-isobutyl-pentylcarbamoyl]-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-benzyloxycarbonylamino-butyric acid benzyl ester