estradiol-17β-O-4-oxobutanoyl-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn

Base Information

• Chemical Name: estradiol-17β-O-4-oxobutanoyl-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn
• CAS No.: 906673-83-4
• Molecular Formula: C₅₈H₇₀N₈O₁₄
• Molecular Weight: 1103.24
• Mol file: 906673-83-4.mol

Synonyms:estradiol-17β-O-4-oxobutanoyl-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn

Chemical Property of estradiol-17β-O-4-oxobutanoyl-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of estradiol-17β-O-4-oxobutanoyl-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn

There total 9 articles about estradiol-17β-O-4-oxobutanoyl-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn 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: 80.3%

Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn hydrochloride + Estradiol-17-hemisuccinate (7698-93-3) → estradiol-17β-O-4-oxobutanoyl-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn (906673-83-4)

Guidance literature:

Estradiol-17-hemisuccinate; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 0.5h; under 750.075 Torr; Inert atmosphere;

Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn hydrochloride; With 4-methyl-morpholine; In tetrahydrofuran; at 0 ℃; under 750.075 Torr; pH=8.5; Inert atmosphere;

DOI:10.1016/j.ejmech.2008.09.036

Reference yield:

H-Asp(Bzl)-Ser(Bzl)-OBzl hydrochloride → estradiol-17β-O-4-oxobutanoyl-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn (906673-83-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1-hydroxybenzotriazole hydrate; N,N'-dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 0 °C

1.2: 91 percent / N-methylmorpholine / tetrahydrofuran / 8 h / 20 °C / pH 8.5

2.1: 93 percent / HCl / ethyl acetate / 2 h / 20 °C

3.1: 1-hydroxybenzotriazole hydrate; N,N'-dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 0 °C

3.2: 89 percent / N-methylmorpholine / tetrahydrofuran / 8 h / 20 °C / pH 8.5

4.1: 93 percent / HCl / ethyl acetate / 3 h / 20 °C

5.1: 1-hydroxybenzotriazole hydrate; N,N'-dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 0 °C

5.2: 61 percent / tetrahydrofuran / 8 h / 20 °C / pH 8.0

With hydrogenchloride; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jm070242a

Reference yield:

H-Gly-Asp(OBzl)-Ser(Bzl)-OBzl*HCl → estradiol-17β-O-4-oxobutanoyl-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn (906673-83-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1-hydroxybenzotriazole hydrate; N,N'-dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 0 °C

1.2: 89 percent / N-methylmorpholine / tetrahydrofuran / 8 h / 20 °C / pH 8.5

2.1: 93 percent / HCl / ethyl acetate / 3 h / 20 °C

3.1: 1-hydroxybenzotriazole hydrate; N,N'-dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 0 °C

3.2: 61 percent / tetrahydrofuran / 8 h / 20 °C / pH 8.0

With hydrogenchloride; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jm070242a

upstream raw materials:

Estradiol-17-hemisuccinate

estradiol

BOC-L-aspartic acid 4-benzyl ester

(S)-benzyl 2-amino-3-(benzyloxy)propanoate hydrochloride

Refernces

• 1、 Zhao, Ming,Liu, Jiangyuan,Zhang, Xiaoyi,Peng, Li,Li, Chunyu,Peng, Shiqi. "3D QSAR of novel estrogen-RGD peptide conjugates: Getting insight into structural dependence of anti-osteoporosis activity and side effect of estrogen in ERT". supporting information; experimental part. p. 3680 - 3689. Retrieved 2009/10/17.