(E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester
• CAS No.: 195325-72-5
• Molecular Formula: C₃₀H₃₈N₂O₉S₂
• Molecular Weight: 634.772
• Mol file: 195325-72-5.mol

Synonyms:(E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester

Chemical Property of (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester

There total 10 articles about (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl 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: 86.0%

methanesulfonyl chloride (124-63-0) + (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester (195325-71-4) → (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester (195325-72-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1248/cpb.45.1259

Reference yield:

Boc-Trp-OH (13139-14-5) → (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester (195325-72-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / 4-dimethylaminopyridine, N,N-dicyclohexylcarbodiimide, N,N-diisopropylethylamine / CH₂Cl₂ / 1.) from -30 to -20 deg C, 2 h, 2.) RT, 16 h

2: 1.) NaH / 1.) DMF, 0 deg C, 2 h, 2.) DMF, a) 0 deg C, 3 h, b) RT, 15 h

3: 1 M DIBAL / toluene; tetrahydrofuran / 1.5 h / -78 °C

4: tetrahydrofuran / 20 h / 0 °C

5: 85 percent / p-toluenesulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

6: 76 percent / tetraethylammonium chloride, AcONa, 70percent aq. tert-butylhydroxyperoxide, OsO₄ / acetone; 2-methyl-propan-2-ol / 120 h / Ambient temperature

7: aq. NaIO₄ / methanol / 5 h / 0 °C

8: CH₂Cl₂ / 1.) 0 deg C, 3 h, 2.) RT, 16 h

9: 85 percent / AcOH-THF-H₂O / 72 h / Ambient temperature

10: 86 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With tetrahydrofuran; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; tetraethylammonium chloride; sodium acetate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; tert-butyl alcohol;

DOI:10.1248/cpb.45.1259

Reference yield:

(S)-tert-butyl (3-(1H-indol-3-yl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate (97530-05-7) → (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester (195325-72-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 2 h, 2.) DMF, a) 0 deg C, 3 h, b) RT, 15 h

2: 1 M DIBAL / toluene; tetrahydrofuran / 1.5 h / -78 °C

3: tetrahydrofuran / 20 h / 0 °C

4: 85 percent / p-toluenesulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

5: 76 percent / tetraethylammonium chloride, AcONa, 70percent aq. tert-butylhydroxyperoxide, OsO₄ / acetone; 2-methyl-propan-2-ol / 120 h / Ambient temperature

6: aq. NaIO₄ / methanol / 5 h / 0 °C

7: CH₂Cl₂ / 1.) 0 deg C, 3 h, 2.) RT, 16 h

8: 85 percent / AcOH-THF-H₂O / 72 h / Ambient temperature

9: 86 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With tetrahydrofuran; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; tetraethylammonium chloride; sodium acetate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; tert-butyl alcohol;

DOI:10.1248/cpb.45.1259

upstream raw materials:

methanesulfonyl chloride

(E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-[1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indol-3-yl]-hex-2-enoic acid methyl ester

Boc-Trp-OH

(S)-tert-butyl (3-(1H-indol-3-yl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate