Hexaaxetylcelenamid A

Base Information

• Chemical Name: Hexaaxetylcelenamid A
• CAS No.: 74144-16-4
• Molecular Formula: C₄₆H₄₈BrN₅O₁₄
• Molecular Weight: 974.816
• Mol file: 74144-16-4.mol

Synonyms:Hexaaxetylcelenamid A

Chemical Property of Hexaaxetylcelenamid A

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hexaaxetylcelenamid A

There total 28 articles about Hexaaxetylcelenamid A 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: 60.0%

<(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) → Hexaaxetylcelenamid A (74144-16-4)

Guidance literature:

With sodium periodate; In 1,4-dioxane; water;

Reference yield:

3,4-(diacetyloxy)benzoyl chloride (57929-25-6) → Hexaaxetylcelenamid A (74144-16-4)

Guidance literature:

Multi-step reaction with 9 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

9: 60 percent / sodium metaperiodate / dioxane; H₂O

With hydrogenchloride; sodium periodate; 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; water;

Reference yield:

6-bromo-N-(tert-butoxycarbonyl)-indole-3-carboxyaldehyde (93862-70-5) → Hexaaxetylcelenamid A (74144-16-4)

Guidance literature:

Multi-step reaction with 8 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

8: 60 percent / sodium metaperiodate / dioxane; H₂O

With sodium periodate; 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 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

acetic anhydride

Celenamide A

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

6-bromo-1H-indole

Downstream raw materials:

2-Acetylamino-4-methyl-pentanoic acid [(Z)-1-[2-(6-bromo-1H-indol-3-yl)-1-carbamoyl-ethylcarbamoyl]-2-(3,4,5-trimethoxy-phenyl)-vinyl]-amide

2-Acetylamino-4-methyl-pentanoic acid [(Z)-1-[2-(6-bromo-1H-indol-3-yl)-1-carbamoyl-ethylcarbamoyl]-2-(3,4,5-trihydroxy-phenyl)-vinyl]-amide

Acetic acid 2,3-diacetoxy-5-{(Z)-2-(2-acetylamino-4-methyl-pentanoylamino)-2-[2-(6-bromo-1H-indol-3-yl)-1-carbamoyl-ethylcarbamoyl]-vinyl}-phenyl ester