cyclo<-D-Pro¹-Phe²-Ala³-Glu(OtBu)⁴-Phe⁵-Phe⁶->

Base Information

• Chemical Name: cyclo<-D-Pro¹-Phe²-Ala³-Glu(OtBu)⁴-Phe⁵-Phe⁶->
• CAS No.: 135481-61-7
• Molecular Formula: C₄₄H₅₄N₆O₈
• Molecular Weight: 794.948
• Mol file: 135481-61-7.mol

Synonyms:cyclo<-D-Pro¹-Phe²-Ala³-Glu(OtBu)⁴-Phe⁵-Phe⁶->

Chemical Property of cyclo<-D-Pro¹-Phe²-Ala³-Glu(OtBu)⁴-Phe⁵-Phe⁶->

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclo<-D-Pro¹-Phe²-Ala³-Glu(OtBu)⁴-Phe⁵-Phe⁶->

There total 11 articles about cyclo<-D-Pro¹-Phe²-Ala³-Glu(OtBu)⁴-Phe⁵-Phe⁶-> 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:

N-Cbz-L-Phe (1161-13-3) → cyclo<-D-Pro1-Phe2-Ala3-Glu(OtBu)4-Phe5-Phe6-> (135481-61-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / NMM, HOBt, EDCI*HCl / tetrahydrofuran / -10 - 20 °C

2: 93 percent / hydrazine monohydrate / methanol / 10 h

3: 1.) 36percent aq. HCl, isopentyl nitrite, 2.) DIPEA / 1.) DMA, -10 deg C, 1.5 h, 2.) DMA, 4 deg C, 12 h

4: hydrazine monohydrate / methanol / 16 h

5: H₂ / 10percent Pd/C / methanol; acetic acid

6: 1.) 36percent aq. HCl, isopentyl nitrite, 2.) DIPEA / 1.) DMF, -10 deg C, 1.5 h, 2.) DMF, 4 deg C, 5 d

With 4-methyl-morpholine; hydrogenchloride; hydrogen; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; isopentyl nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; acetic acid;

DOI:10.1021/ja00020a016

Reference yield:

5-tert-butyl N-benzyloxycarbonyl-L-glutamate (3886-08-6) → cyclo<-D-Pro1-Phe2-Ala3-Glu(OtBu)4-Phe5-Phe6-> (135481-61-7)

Guidance literature:

Multi-step reaction with 8 steps

1: NMM / tetrahydrofuran / 1 h / -10 - 20 °C

2: H₂ / 10percent Pd/C / methanol

3: N,N-dimethyl-acetamide

4: H₂ / 10percent Pd/C / methanol

5: 1.) 36percent aq. HCl, isopentyl nitrite, 2.) DIPEA / 1.) DMA, -10 deg C, 1.5 h, 2.) DMA, 4 deg C, 12 h

6: hydrazine monohydrate / methanol / 16 h

7: H₂ / 10percent Pd/C / methanol; acetic acid

8: 1.) 36percent aq. HCl, isopentyl nitrite, 2.) DIPEA / 1.) DMF, -10 deg C, 1.5 h, 2.) DMF, 4 deg C, 5 d

With 4-methyl-morpholine; hydrogenchloride; hydrogen; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; isopentyl nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl acetamide; acetic acid;

DOI:10.1021/ja00020a016

Reference yield:

H-Glu(OtBu)-Phe-OMe (135481-70-8) → cyclo<-D-Pro1-Phe2-Ala3-Glu(OtBu)4-Phe5-Phe6-> (135481-61-7)

Guidance literature:

Multi-step reaction with 6 steps

1: N,N-dimethyl-acetamide

2: H₂ / 10percent Pd/C / methanol

3: 1.) 36percent aq. HCl, isopentyl nitrite, 2.) DIPEA / 1.) DMA, -10 deg C, 1.5 h, 2.) DMA, 4 deg C, 12 h

4: hydrazine monohydrate / methanol / 16 h

5: H₂ / 10percent Pd/C / methanol; acetic acid

6: 1.) 36percent aq. HCl, isopentyl nitrite, 2.) DIPEA / 1.) DMF, -10 deg C, 1.5 h, 2.) DMF, 4 deg C, 5 d

With hydrogenchloride; hydrogen; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; isopentyl nitrite; palladium on activated charcoal; In methanol; N,N-dimethyl acetamide; acetic acid;

DOI:10.1021/ja00020a016

upstream raw materials:

H-Phe-D-Pro-Phe-Ala-Glu(OtBu)-Phe-NHNH₂*2HOAc

N-Cbz-L-Phe

5-tert-butyl N-benzyloxycarbonyl-L-glutamate

H-Glu(OtBu)-Phe-OMe

Downstream raw materials:

cyclo<-D-Pro¹-Phe²-Ala³-Gln⁴-Phe⁵-Phe⁶->

cyclo<-D-Pro¹-Phe²-Ala³-Gln⁴-Phe⁵-Phe⁶->

cyclo<-D-Pro¹-Phe²-Ala³-Glu⁴-Phe⁵-Phe⁶->