2-[[[(6S)-1-[(3S)-N-(2-Hydroxymethyl Ser-L-Ala-)-3-amino-L-Abu-]-1,4,5,6-tetrahydropyridazin-6-yl]carbonyl-L-Leu-]amino]-3-methyl-2-butenoyl-L-Ser-OH

Base Information

• Chemical Name: 2-[[[(6S)-1-[(3S)-N-(2-Hydroxymethyl Ser-L-Ala-)-3-amino-L-Abu-]-1,4,5,6-tetrahydropyridazin-6-yl]carbonyl-L-Leu-]amino]-3-methyl-2-butenoyl-L-Ser-OH
• CAS No.: 82518-59-0
• Molecular Formula: C₃₀H₅₁N₉O₁₁
• Molecular Weight: 713.789
• Mol file: 82518-59-0.mol

Synonyms:

Chemical Property of 2-[[[(6S)-1-[(3S)-N-(2-Hydroxymethyl Ser-L-Ala-)-3-amino-L-Abu-]-1,4,5,6-tetrahydropyridazin-6-yl]carbonyl-L-Leu-]amino]-3-methyl-2-butenoyl-L-Ser-OH

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[[[(6S)-1-[(3S)-N-(2-Hydroxymethyl Ser-L-Ala-)-3-amino-L-Abu-]-1,4,5,6-tetrahydropyridazin-6-yl]carbonyl-L-Leu-]amino]-3-methyl-2-butenoyl-L-Ser-OH

There total 29 articles about 2-[[[(6S)-1-[(3S)-N-(2-Hydroxymethyl Ser-L-Ala-)-3-amino-L-Abu-]-1,4,5,6-tetrahydropyridazin-6-yl]carbonyl-L-Leu-]amino]-3-methyl-2-butenoyl-L-Ser-OH 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:

2-(tert-butoxycarbonylhydrazono)-5,5-(1,3-propanediyldioxy)pentanoic acid (152499-68-8) → antrimycin Dv (82518-59-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 98 percent / CH₂Cl₂ / 0.08 h / Ambient temperature

2: 98 percent / NaCNBH₃, AcOH / acetonitrile / 24 h / Ambient temperature

3: collidine / tetrahydrofuran / 18 h / 0 - 20 °C

4: TFA / 2 h / Ambient temperature

5: 1.) aq. NaOH, 2.) aq. H₂SO₄ / 1.) dioxane, RT, 14 h, 2.) dioxane, RT, 5 min

6: NaHCO₃ / H₂O; dioxane / 16 h / Ambient temperature

7: H₂ / Pd/C / dioxane / 3 h / Ambient temperature

8: pyridine / CH₂Cl₂ / 15 h / 0 - 20 °C

9: 100 percent / aq. NaOH / dioxane / 14 h / Ambient temperature

10: 68 percent / i-Pr₂NEt, diphenyl phosphorylazide / CH₂Cl₂ / 1.) -20 deg C, 1 h, 2.) 4 deg C, 3 d

11: 100 percent / HCl / dioxane / 2 h / 5 - 20 °C

12: 47 percent / dimethylaminopyridine (DMAP) / tetrahydrofuran / 16 h / Ambient temperature

13: Pd(PPh₃)4, morpholine / tetrahydrofuran / 2 h / Ambient temperature

14: HCl / dioxane / 2 h / Ambient temperature

With morpholine; pyridine; 2,3,5-trimethyl-pyridine; hydrogenchloride; dmap; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; diphenyl phosphoryl azide; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;

DOI:10.1039/c39920001186

Reference yield:

methyl 2-(tert-butoxycarbonylhydrazono)-5,5-(1,3-propanediyldioxy)pentanoate (152499-66-6) → antrimycin Dv (82518-59-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 98 percent / NaCNBH₃, AcOH / acetonitrile / 24 h / Ambient temperature

2: collidine / tetrahydrofuran / 18 h / 0 - 20 °C

3: TFA / 2 h / Ambient temperature

4: 1.) aq. NaOH, 2.) aq. H₂SO₄ / 1.) dioxane, RT, 14 h, 2.) dioxane, RT, 5 min

5: NaHCO₃ / H₂O; dioxane / 16 h / Ambient temperature

6: H₂ / Pd/C / dioxane / 3 h / Ambient temperature

7: pyridine / CH₂Cl₂ / 15 h / 0 - 20 °C

8: 100 percent / aq. NaOH / dioxane / 14 h / Ambient temperature

9: 68 percent / i-Pr₂NEt, diphenyl phosphorylazide / CH₂Cl₂ / 1.) -20 deg C, 1 h, 2.) 4 deg C, 3 d

10: 100 percent / HCl / dioxane / 2 h / 5 - 20 °C

11: 47 percent / dimethylaminopyridine (DMAP) / tetrahydrofuran / 16 h / Ambient temperature

12: Pd(PPh₃)4, morpholine / tetrahydrofuran / 2 h / Ambient temperature

13: HCl / dioxane / 2 h / Ambient temperature

With morpholine; pyridine; 2,3,5-trimethyl-pyridine; hydrogenchloride; dmap; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; diphenyl phosphoryl azide; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;

DOI:10.1039/c39920001186

Reference yield:

ethyl (E/Z)-2-(tert-butoxycarbonylhydrazono)-5,5-(1,3-propanediyldioxy)pentanoate → antrimycin Dv (82518-59-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 86 percent / aq. NaOH / dioxane / 4 h / Ambient temperature

2: 98 percent / CH₂Cl₂ / 0.08 h / Ambient temperature

3: 98 percent / NaCNBH₃, AcOH / acetonitrile / 24 h / Ambient temperature

4: collidine / tetrahydrofuran / 18 h / 0 - 20 °C

5: TFA / 2 h / Ambient temperature

6: 1.) aq. NaOH, 2.) aq. H₂SO₄ / 1.) dioxane, RT, 14 h, 2.) dioxane, RT, 5 min

7: NaHCO₃ / H₂O; dioxane / 16 h / Ambient temperature

8: H₂ / Pd/C / dioxane / 3 h / Ambient temperature

9: pyridine / CH₂Cl₂ / 15 h / 0 - 20 °C

10: 100 percent / aq. NaOH / dioxane / 14 h / Ambient temperature

11: 68 percent / i-Pr₂NEt, diphenyl phosphorylazide / CH₂Cl₂ / 1.) -20 deg C, 1 h, 2.) 4 deg C, 3 d

12: 100 percent / HCl / dioxane / 2 h / 5 - 20 °C

13: 47 percent / dimethylaminopyridine (DMAP) / tetrahydrofuran / 16 h / Ambient temperature

14: Pd(PPh₃)4, morpholine / tetrahydrofuran / 2 h / Ambient temperature

15: HCl / dioxane / 2 h / Ambient temperature

With morpholine; pyridine; 2,3,5-trimethyl-pyridine; hydrogenchloride; dmap; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; diphenyl phosphoryl azide; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;

DOI:10.1039/c39920001186

upstream raw materials:

Methyl 2-[(S)-2-tert-butoxycarbonylamino-4-methylpentanoylamino]-2-(dimethoxyphosphoryl)acetate

methyl 2-<(S)-2-tert-butoxycarbonylamino-4-methylpentanoylamino>-3-methyl-2-butenoate

2-(tert-butoxycarbonylhydrazono)-5,5-(1,3-propanediyldioxy)pentanoic acid

2-<(S)-2-tert-butoxycarbonylamino-4-methylpentanoylamino>-3-methyl-2-butenoic acid

Refernces

• 1、 Schmidt,Riedl. "The total synthesis of antrimycin D(v)". . p. 1186 - 1187. Retrieved 2007/10/02.