PESTAHIVIN

Base Information

• Chemical Name: PESTAHIVIN
• CAS No.: 165754-55-2
• Molecular Formula: C53H84 N8 O9
• Molecular Weight: 977.294
• Mol file: 165754-55-2.mol

Synonyms:L-Alanine,N-[2-[(4-cyano-2-hydroxy-1-oxobutyl)amino]-4-methyl-1-oxooctyl]-N-methyl-L-leucyl-L-leucyl-1-methoxy-N-methyl-L-tryptophyl-4-methyl-L-2-aminooctanoyl-N-methyl-,t-lactone; HUN 7293; Pestahivin

Chemical Property of PESTAHIVIN

Chemical Property:

• PSA: 212.48000
• LogP: 6.75178

Purity/Quality:

PESTAHIVIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of PESTAHIVIN

There total 49 articles about PESTAHIVIN 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:

(4R)-4-methyl-6-hydroxyhexan-1-al (180908-43-4) → HUN-7293 (165754-55-2)

Guidance literature:

Multi-step reaction with 13 steps

2: 94 percent / H₂ / Pd/C

3: 90 percent / Dess-Martin reagent

4: 74 percent / CHCl₃ / 16 h / -25 °C

5: Pb(OAc)4 / 0.17 h / 0 °C

6: aq. HCl / Heating

7: NaHCO₃

8: 54 percent / NaHCO₃, HOAt, EDCI / CH₂Cl₂; dimethylformamide / 32 h / 22 °C

9: HCO₂H / 1 h / 22 °C

10: NaHCO₃, HOAt, EDCI / CH₂Cl₂; dimethylformamide / 2 h / 0 °C

11: Ph₃P, DIAD / toluene / 16 h / 22 °C

12: TFA, anisole / 1 h / 22 °C

13: 2,6-collidine, HATU / CH₂Cl₂ / 10 h / 25 °C

With 2,4,6-trimethyl-pyridine; lead(IV) acetate; hydrogenchloride; formic acid; 1-hydroxy-7-aza-benzotriazole; di-isopropyl azodicarboxylate; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; methoxybenzene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja990918u

Reference yield:

(3R)-citronellol (1117-61-9) → HUN-7293 (165754-55-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) O₃, 2.) Me₂S / 1.) -78 deg C

3: 94 percent / H₂ / Pd/C

4: 90 percent / Dess-Martin reagent

5: 74 percent / CHCl₃ / 16 h / -25 °C

6: Pb(OAc)4 / 0.17 h / 0 °C

7: aq. HCl / Heating

8: NaHCO₃

9: 54 percent / NaHCO₃, HOAt, EDCI / CH₂Cl₂; dimethylformamide / 32 h / 22 °C

10: HCO₂H / 1 h / 22 °C

11: NaHCO₃, HOAt, EDCI / CH₂Cl₂; dimethylformamide / 2 h / 0 °C

12: Ph₃P, DIAD / toluene / 16 h / 22 °C

13: TFA, anisole / 1 h / 22 °C

14: 2,6-collidine, HATU / CH₂Cl₂ / 10 h / 25 °C

With 2,4,6-trimethyl-pyridine; lead(IV) acetate; hydrogenchloride; formic acid; 1-hydroxy-7-aza-benzotriazole; dimethylsulfide; di-isopropyl azodicarboxylate; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; ozone; methoxybenzene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja990918u

Reference yield:

(R)-3-methyl-6-hepten-1-ol (237431-14-0) → HUN-7293 (165754-55-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 94 percent / H₂ / Pd/C

2: 90 percent / Dess-Martin reagent

3: 74 percent / CHCl₃ / 16 h / -25 °C

4: Pb(OAc)4 / 0.17 h / 0 °C

5: aq. HCl / Heating

6: NaHCO₃

7: 54 percent / NaHCO₃, HOAt, EDCI / CH₂Cl₂; dimethylformamide / 32 h / 22 °C

8: HCO₂H / 1 h / 22 °C

9: NaHCO₃, HOAt, EDCI / CH₂Cl₂; dimethylformamide / 2 h / 0 °C

10: Ph₃P, DIAD / toluene / 16 h / 22 °C

11: TFA, anisole / 1 h / 22 °C

12: 2,6-collidine, HATU / CH₂Cl₂ / 10 h / 25 °C

With 2,4,6-trimethyl-pyridine; lead(IV) acetate; hydrogenchloride; formic acid; 1-hydroxy-7-aza-benzotriazole; di-isopropyl azodicarboxylate; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; methoxybenzene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja990918u

upstream raw materials:

3-[(3S,6S,9S,12R,15S,18S)-18,21-Diisobutyl-3-(1-methoxy-1H-indol-3-ylmethyl)-2,8,9,17-tetramethyl-6,15-bis-((R)-2-methyl-hexyl)-4,7,10,13,16-pentaoxo-11,22-dioxa-2,5,8,14,17,20-hexaaza-bicyclo[17.2.1]docosa-1⁽²¹⁾,19-dien-12-yl]-propionitrile

N-<(2S,4R)-2-1'-methoxy-N-methyl-L-tryptophanyl>amino>-4-methylheptanoyl>-N-methyl-L-alanyloxy>-4-cyanobutanoyl>amino-4-methylheptanoyl>-N-methyl-L-leucine

N-tert-butoxycarbonyl-L-leucine

tert-butyl (2S)-4-methyl-2-(methylamino)pentanoate

Refernces

• 1、 Chen, Yan,Bilban, Melitta,Foster, Carolyn A.,Boger, Dale L.. "Solution-phase parallel synthesis of a pharmacophore library of HUN-7293 analogues: A general chemical mutagenesis approach to defining structure-function properties of naturally occurring cyclic (depsi)peptides". . p. 5431 - 5440. Retrieved 2007/10/03.