(Z)-D-Ser{Fmoc-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OTce

Base Information

• Chemical Name: (Z)-D-Ser{Fmoc-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OTce
• CAS No.: 713122-17-9
• Molecular Formula: C₆₄H₈₅Cl₃N₁₀O₁₉S₂
• Molecular Weight: 1468.93
• Mol file: 713122-17-9.mol

Synonyms:(Z)-D-Ser{Fmoc-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OTce

Chemical Property of (Z)-D-Ser{Fmoc-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OTce

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-D-Ser{Fmoc-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OTce

There total 17 articles about (Z)-D-Ser{Fmoc-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OTce 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: 52.0%

(Z)-D-Ser[L-Ala-L-Cys(Acm)-L-Val]-OTce (713122-04-4) + Fmoc-D-Ser[N-Boc-L-Ala-L-Cys(Acm)-L-Val]-OH (713122-16-8) → (Z)-D-Ser{Fmoc-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OTce (713122-17-9)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 18h;

DOI:10.1021/jo0496805

Reference yield:

(R)-2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoic acid (65806-90-8) → (Z)-D-Ser{Fmoc-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OTce (713122-17-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 78 percent / pyridine; HOBt; DCC / 18 h / 0 °C

2: 76 percent / TFA / 0.75 h / 10 °C

3: 88 percent / pyridine; HOBt; DCC / 18 h / 0 °C

4: TFA / 0.5 h / 25 °C

5: 3.80 g / HOAt; EDCI / CH₂Cl₂ / 18 h / 0 °C

6: TFA / 0.5 h / 25 °C

7: 3.18 g / HOAt; EDCI / CH₂Cl₂ / 16 h / 0 °C

8: TFA / 0.5 h / 25 °C

9: 52 percent / HOAt; EDCI / CH₂Cl₂ / 18 h / 0 °C

With pyridine; 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo0496805

Reference yield:

Nα-(9-fluorenylmethoxycarbonyl)-D-serine-tert-butyl ether (71989-33-8,128107-47-1) → (Z)-D-Ser{Fmoc-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OTce (713122-17-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 66 percent / pyridine; HOBt; DCC / 18 h / 0 °C

2: 72 percent / TFA / 0.75 h / 10 °C

3: 73 percent / pyridine; HOBt; DCC / 18 h / 0 °C

4: TFA / 0.5 h / 25 °C

5: 2.06 g / HOAt; EDCI / CH₂Cl₂ / 18 h / 0 °C

6: TFA / 0.5 h / 25 °C

7: 1.41 g / HOAt; EDCI / CH₂Cl₂ / 16 h / 0 °C

8: 91 percent / aq. AcOH; Zn powder / 2.5 h / 0 °C

9: 52 percent / HOAt; EDCI / CH₂Cl₂ / 18 h / 0 °C

With pyridine; 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; In dichloromethane;

DOI:10.1021/jo0496805

upstream raw materials:

(Z)-D-Ser[L-Ala-L-Cys(Acm)-L-Val]-OTce

Fmoc-D-Ser[N-Boc-L-Ala-L-Cys(Acm)-L-Val]-OH

(R)-2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoic acid

Nα-(9-fluorenylmethoxycarbonyl)-D-serine-tert-butyl ether

Downstream raw materials:

[(1R,4S,7R,11S,14R,17S,20R,24S)-20-(9H-Fluoren-9-ylmethoxycarbonylamino)-11,24-diisopropyl-4,17-dimethyl-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexaaza-bicyclo[12.12.4]triacont-7-yl]-carbamic acid benzyl ester

C₅₆H₇₂N₈O₁₇S₂

(Z)-D-Ser{Fmoc-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OH