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

Base Information

Chemical Name:cyclo<-D-Pro¹-Phe²-Ala³-Gln⁴-Phe⁵-Phe⁶->
CAS No.:135481-69-5
Molecular Formula:C₅₄H₆₆N₈O₁₅
Molecular Weight:1067.16
Hs Code.:

cyclo<-D-Pro<sup>1</sup>-Phe<sup>2</sup>-Ala<sup>3</sup>-<N-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)>Gln<sup>4</sup>-Phe<sup>5</sup>-Phe<sup>6</sup>->

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

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Chemical Property of cyclo<-D-Pro¹-Phe²-Ala³-Gln⁴-Phe⁵-Phe⁶->

Chemical Property:

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Technology Process of cyclo<-D-Pro¹-Phe²-Ala³-Gln⁴-Phe⁵-Phe⁶->

There total 13 articles about cyclo<-D-Pro¹-Phe²-Ala³-Gln⁴-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:

: 1161-13-3
N-Cbz-L-Phe

: 135481-69-5
cyclo<-D-Pro¹-Phe²-Ala³-Gln⁴-Phe⁵-Phe⁶->

Guidance literature:: Multi-step reaction with 8 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

7: 100 percent / gaseous HCl / diethyl ether / 0.5 h

8: 1.) HOBt, EDCI, 2.) EDCI / 1.) THF, -15 deg C, 1 h, 2.) THF, RT deg C, 8 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; diethyl ether; acetic acid;
DOI:10.1021/ja00020a016

Reference yield:

: 3886-08-6
5-tert-butyl N-benzyloxycarbonyl-L-glutamate

: 135481-69-5
cyclo<-D-Pro¹-Phe²-Ala³-Gln⁴-Phe⁵-Phe⁶->

Guidance literature:: Multi-step reaction with 10 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

9: 100 percent / gaseous HCl / diethyl ether / 0.5 h

10: 1.) HOBt, EDCI, 2.) EDCI / 1.) THF, -15 deg C, 1 h, 2.) THF, RT deg C, 8 d

With 4-methyl-morpholine; hydrogenchloride; hydrogen; benzotriazol-1-ol; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; isopentyl nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl acetamide; acetic acid;
DOI:10.1021/ja00020a016

Reference yield:

: 135481-70-8
H-Glu(OtBu)-Phe-OMe

: 135481-69-5
cyclo<-D-Pro¹-Phe²-Ala³-Gln⁴-Phe⁵-Phe⁶->

Guidance literature:: Multi-step reaction with 8 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

7: 100 percent / gaseous HCl / diethyl ether / 0.5 h

8: 1.) HOBt, EDCI, 2.) EDCI / 1.) THF, -15 deg C, 1 h, 2.) THF, RT deg C, 8 d

With hydrogenchloride; hydrogen; benzotriazol-1-ol; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; isopentyl nitrite; palladium on activated charcoal; In methanol; diethyl ether; N,N-dimethyl acetamide; acetic acid;
DOI:10.1021/ja00020a016