Vasoactive intestinal peptide (22-28)

Base Information

• Chemical Name: Vasoactive intestinal peptide (22-28)
• CAS No.: 47900-24-3
• Molecular Formula: C38H62N10O11
• Molecular Weight: 834.96
• Mol file: 47900-24-3.mol

Synonyms:l-tyrosyl-l-leucyl-l-asparaginyl-l-seryl-l-isoleucyl-l-leucyl-l-aspartamide;Tyr-leu-asp-ser-ile-leu-asp-amide;

Chemical Property of Vasoactive intestinal peptide (22-28)

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1330°C at 760 mmHg
• Flash Point: 758.1°C
• PSA: 394.26000
• Density: 1.267g/cm³
• LogP: 5.72870

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Vasoactive intestinal peptide (22-28)

There total 15 articles about Vasoactive intestinal peptide (22-28) 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:

Z(OMe)-Ile-OH (47174-55-0) → (S)-2-[(S)-2-((S)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoylamino}-3-carbamoyl-propionylamino)-3-hydroxy-propionylamino]-3-methyl-pentanoic acid [(S)-1-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-3-methyl-butyl]-amide (47900-24-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) Et₃N, 2) DCC / 2) DMF, THF, 24 h

2: 80percent hydrazine hydrate / methanol

3: diazotizing reagent

4: 90 percent / Et₃N / dimethylsulfoxide; hexamethylphosphoric acid triamide / 40 h / 4 °C

5: 90 percent / Et₃N / dimethylsulfoxide; hexamethylphosphoric acid triamide / 40 h / 4 °C

6: TFA, anisole

7: 77 percent / Et₃N / dimethylsulfoxide; hexamethylphosphoric acid triamide / 24 h / 40 °C

8: TFA, anisole

With diazotizing reagent; hydrazine hydrate; methoxybenzene; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dimethyl sulfoxide;

DOI:10.1248/cpb.28.1873

Reference yield:

methyl (L)-leucinate hydrochloride (7517-19-3) → (S)-2-[(S)-2-((S)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoylamino}-3-carbamoyl-propionylamino)-3-hydroxy-propionylamino]-3-methyl-pentanoic acid [(S)-1-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-3-methyl-butyl]-amide (47900-24-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) Et₃N, 2) DCC / 2) DMF, THF, 24 h

2: 80percent hydrazine hydrate / methanol

3: diazotizing reagent

4: 90 percent / Et₃N / dimethylsulfoxide; hexamethylphosphoric acid triamide / 40 h / 4 °C

5: 90 percent / Et₃N / dimethylsulfoxide; hexamethylphosphoric acid triamide / 40 h / 4 °C

6: TFA, anisole

7: 77 percent / Et₃N / dimethylsulfoxide; hexamethylphosphoric acid triamide / 24 h / 40 °C

8: TFA, anisole

With diazotizing reagent; hydrazine hydrate; methoxybenzene; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dimethyl sulfoxide;

DOI:10.1248/cpb.28.1873

Reference yield:

Z(OMe)-Ile-Leu-OMe (75720-24-0) → (S)-2-[(S)-2-((S)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoylamino}-3-carbamoyl-propionylamino)-3-hydroxy-propionylamino]-3-methyl-pentanoic acid [(S)-1-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-3-methyl-butyl]-amide (47900-24-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 80percent hydrazine hydrate / methanol

2: diazotizing reagent

3: 90 percent / Et₃N / dimethylsulfoxide; hexamethylphosphoric acid triamide / 40 h / 4 °C

4: 90 percent / Et₃N / dimethylsulfoxide; hexamethylphosphoric acid triamide / 40 h / 4 °C

5: TFA, anisole

6: 77 percent / Et₃N / dimethylsulfoxide; hexamethylphosphoric acid triamide / 24 h / 40 °C

7: TFA, anisole

With diazotizing reagent; hydrazine hydrate; methoxybenzene; triethylamine; trifluoroacetic acid; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dimethyl sulfoxide;

DOI:10.1248/cpb.28.1873

upstream raw materials:

Z(OMe)-(porcine VIP 22-28)-NH₂

Z(OMe)-Ile-OH

methyl (L)-leucinate hydrochloride

Z(OMe)-Ile-Leu-OMe

Downstream raw materials:

Z(OMe)-Lys(Z)-Lys(Z)-Tyr-Leu-Asn-Ser-Ile-Leu-Asn-NH₂

Z(OMe)-Ala-Val-Lys-(Z)-Lys(Z)-Tyr-Leu-Asn-Ser-Ile-Leu-Asn-NH₂

Refernces