<(S)-N-Acetylleucyl>-<(Z)-3,4,5-triacetoxy-α,β-didehydrophenylalanyl>-<(S)-6-brom-N-<2-(3,4-diacetoxyphenyl)-2-(4-nitrophenylseleno)ethyl>tryptophanamid>

Base Information

• Chemical Name: <(S)-N-Acetylleucyl>-<(Z)-3,4,5-triacetoxy-α,β-didehydrophenylalanyl>-<(S)-6-brom-N-<2-(3,4-diacetoxyphenyl)-2-(4-nitrophenylseleno)ethyl>tryptophanamid>
• CAS No.: 93862-80-7
• Molecular Formula: C₅₂H₅₃BrN₆O₁₆Se
• Molecular Weight: 1176.89
• Mol file: 93862-80-7.mol

Synonyms:

Chemical Property of <(S)-N-Acetylleucyl>-<(Z)-3,4,5-triacetoxy-α,β-didehydrophenylalanyl>-<(S)-6-brom-N-<2-(3,4-diacetoxyphenyl)-2-(4-nitrophenylseleno)ethyl>tryptophanamid>

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <(S)-N-Acetylleucyl>-<(Z)-3,4,5-triacetoxy-α,β-didehydrophenylalanyl>-<(S)-6-brom-N-<2-(3,4-diacetoxyphenyl)-2-(4-nitrophenylseleno)ethyl>tryptophanamid>

There total 25 articles about <(S)-N-Acetylleucyl>-<(Z)-3,4,5-triacetoxy-α,β-didehydrophenylalanyl>-<(S)-6-brom-N-<2-(3,4-diacetoxyphenyl)-2-(4-nitrophenylseleno)ethyl>tryptophanamid> 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:

3,4-(diacetyloxy)benzoyl chloride (57929-25-6) → <(S)-N-Acetylleucyl>-<(Z)-3,4,5-triacetoxy-α,β-didehydrophenylalanyl>-<(S)-6-brom-N-<2-(3,4-diacetoxyphenyl)-2-(4-nitrophenylseleno)ethyl>tryptophanamid> (93862-80-7,100993-01-9)

Guidance literature:

Multi-step reaction with 8 steps

1: TEA / dioxane

2: 2 N etheric HCl / dioxane / 0.25 h / 20 °C

3: 1.) KI; 2.) NaN₃ / 1.) acetone, 15 min; acetone, 6 h, room temp.

4: 83 percent / H₂ / Pd/C (5percent Pd) / dioxane / 18 h / 2206.5 Torr

5: 97 percent / acetic acid, sodium-cyano trihydroborate / tetrahydrofuran / 4 h / 25 °C

6: 78 percent / tributyl phosphine / tetrahydrofuran / 3 h

7: 94 percent / 1,3-dimethoxy benzene, HCl-gas / dioxane / 1 h / Ambient temperature

8: 1.) TEA; 2.) N-hydroxy succinimide, N,N'-dicyclohexylcarbodiimide / 1.) acetonitrile; 2.) acetonotrile, -10 deg C - room temp., 3 h; then room temp., 10 h

With hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; sodium azide; tributylphosphine; TEA; hydrogen; sodium cyanoborohydride; acetic acid; dicyclohexyl-carbodiimide; potassium iodide; 1,3-Dimethoxybenzene; 5%-palladium/activated carbon; In tetrahydrofuran; 1,4-dioxane;

Reference yield:

6-bromo-N-(tert-butoxycarbonyl)-indole-3-carboxyaldehyde (93862-70-5) → <(S)-N-Acetylleucyl>-<(Z)-3,4,5-triacetoxy-α,β-didehydrophenylalanyl>-<(S)-6-brom-N-<2-(3,4-diacetoxyphenyl)-2-(4-nitrophenylseleno)ethyl>tryptophanamid> (93862-80-7,100993-01-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) KOC(CH₃)3 / 1.) CH₂Cl₂, -60 deg C; 2.) CH₂Cl₂, 2 h

2: H₂ / ⁽¹⁺⁾*BF₄^(1-) / ethanol / 20 h / 2206.5 Torr

3: 1-piperidine carbothioamide, acetic acid / ethanol / 3.5 h / Heating

4: 69 percent / N,N'-dicyclohexyl carbodiimide / dimethylformamide; acetonitrile / 18 h / Ambient temperature

5: 1.) LiN(iPr)2 / 1.) THF, -60 to -10 deg C; 2.) THF, 2 h

6: formic acid / 1.5 h / 40 °C

7: 1.) TEA; 2.) N-hydroxy succinimide, N,N'-dicyclohexylcarbodiimide / 1.) acetonitrile; 2.) acetonotrile, -10 deg C - room temp., 3 h; then room temp., 10 h

With 1-hydroxy-pyrrolidine-2,5-dione; formic acid; TEA; potassium tert-butylate; hydrogen; piperidine-1-carbothioamide; acetic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide; (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl) phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; In ethanol; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

(Z)-3-<6-Brom-1-(tert-butyloxycarbonyl)-3-indolyl>-2-(chloracetylamino)acrylsaeure-tert-butylester (93862-72-7) → <(S)-N-Acetylleucyl>-<(Z)-3,4,5-triacetoxy-α,β-didehydrophenylalanyl>-<(S)-6-brom-N-<2-(3,4-diacetoxyphenyl)-2-(4-nitrophenylseleno)ethyl>tryptophanamid> (93862-80-7,100993-01-9)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / ⁽¹⁺⁾*BF₄^(1-) / ethanol / 20 h / 2206.5 Torr

2: 1-piperidine carbothioamide, acetic acid / ethanol / 3.5 h / Heating

3: 69 percent / N,N'-dicyclohexyl carbodiimide / dimethylformamide; acetonitrile / 18 h / Ambient temperature

4: 1.) LiN(iPr)2 / 1.) THF, -60 to -10 deg C; 2.) THF, 2 h

5: formic acid / 1.5 h / 40 °C

6: 1.) TEA; 2.) N-hydroxy succinimide, N,N'-dicyclohexylcarbodiimide / 1.) acetonitrile; 2.) acetonotrile, -10 deg C - room temp., 3 h; then room temp., 10 h

With 1-hydroxy-pyrrolidine-2,5-dione; formic acid; TEA; hydrogen; piperidine-1-carbothioamide; acetic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide; (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl) phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; In ethanol; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

Acetic acid 2-acetoxy-5-[2-amino-1-(4-nitro-phenylselanyl)-ethyl]-phenyl ester; hydrochloride

<(S)-N-Acetylleucyl>-<(Z)-3,4,5-triacetoxy-α,β-didehydrophenylalanyl>-<(S)-6-bromtryptophan>

6-bromo-1H-indole

3,4-(diacetyloxy)benzoyl chloride

Downstream raw materials:

Hexaaxetylcelenamid A