(E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid

Base Information

• Chemical Name: (E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid
• CAS No.: 199005-74-8
• Molecular Formula: C₃₁H₃₄N₂O₅
• Molecular Weight: 514.621
• Mol file: 199005-74-8.mol

Synonyms:(E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid

Chemical Property of (E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid

There total 5 articles about (E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid 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: 98.0%

(S,E)-ethyl 4-(tert-butoxycarbonylamino)-7-oxo-7-(tritylamino)-hept-2-enoate (199005-58-8) → (E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid (199005-74-8)

Guidance literature:

With sodium hydroxide; In ethanol; at 23 ℃; for 3h;

DOI:10.1021/jm980068d

Reference yield:

Boc-L-Gln(Trt)-OH (132388-69-3,210750-95-1) → (E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid (199005-74-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 4-methylmorpholine / CH₂Cl₂ / 0.33 h / 0 °C

2: CH₂Cl₂ / 1.) 0 deg C, 20 min, 2.) RT, 2 h

3: diisobutylaluminum hydride / toluene / 4 h / -78 °C

4: 1.) NaN(TMS)2 / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 2 h, b) from -78 deg C to 0 deg C, 10 min

5: 98 percent / aq. NaOH / ethanol / 3 h / 23 °C

With 4-methyl-morpholine; sodium hydroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; In ethanol; dichloromethane; toluene;

DOI:10.1021/jm980068d

Reference yield:

[(S)-1-(Methoxy-methyl-carbamoyl)-3-(trityl-carbamoyl)-propyl]-carbamic acid tert-butyl ester (199005-56-6) → (E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid (199005-74-8)

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminum hydride / toluene / 4 h / -78 °C

2: 1.) NaN(TMS)2 / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 2 h, b) from -78 deg C to 0 deg C, 10 min

3: 98 percent / aq. NaOH / ethanol / 3 h / 23 °C

With sodium hydroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; In ethanol; toluene;

DOI:10.1021/jm980068d

upstream raw materials:

(S,E)-ethyl 4-(tert-butoxycarbonylamino)-7-oxo-7-(tritylamino)-hept-2-enoate

Boc-L-Gln(Trt)-OH

[(S)-1-(Methoxy-methyl-carbamoyl)-3-(trityl-carbamoyl)-propyl]-carbamic acid tert-butyl ester

Boc-Gln(Trt)-H

Downstream raw materials:

(E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid 2,2-dimethyl-propyl ester

(E)-(S)-4-tert-Butoxycarbonylamino-6-(trityl-carbamoyl)-hex-2-enoic acid cyclopentyl ester

[(S)-3-Methyl-1-((S)-1-{(E)-(S)-4-oxo-4-[6-(pyrrolidine-1-sulfonyl)-2,3-dihydro-indol-1-yl]-1-[2-(trityl-carbamoyl)-ethyl]-but-2-enylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butyl]-carbamic acid benzyl ester

[(S)-1-((S)-1-{(E)-(S)-4-(6-Methanesulfonyl-2,3-dihydro-indol-1-yl)-4-oxo-1-[2-(trityl-carbamoyl)-ethyl]-but-2-enylcarbamoyl}-2-phenyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester