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

Base Information

• Chemical Name: (Z)-D-Ser{(Z)-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OH
• CAS No.: 713122-06-6
• Molecular Formula: C₅₅H₈₀N₁₀O₁₉S₂
• Molecular Weight: 1249.43
• Mol file: 713122-06-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (Z)-D-Ser{(Z)-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OH 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: 95.0%

(Z)-D-Ser{(Z)-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OTce (713122-05-5) → (Z)-D-Ser{(Z)-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OH (713122-06-6)

Guidance literature:

With acetic acid; zinc; at 0 ℃; for 2.5h;

DOI:10.1021/jo0496805

Reference yield: 93.0%

N-benzyloxycarbonyl-O--D-serine p-bromophenacyl ester (82667-04-7) → (Z)-D-Ser{(Z)-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OH (713122-06-6)

Guidance literature:

With acetic acid; zinc; 1.) 0 deg C, 2 h, 2.) room temperature, 3 h;

DOI:10.1016/0040-4020(82)85045-X

Reference yield:

(R)-2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoic acid (65806-90-8) → (Z)-D-Ser{(Z)-D-Ser[Boc-L-Ala-L-Cys(Acm)-L-Val]-L-Ala-L-Cys(Acm)-L-Val}-OH (713122-06-6)

Guidance literature:

Multi-step reaction with 10 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: 93 percent / aq. AcOH; Zn powder / 2.5 h / 0 °C

9: 65 percent / HOAt; EDCI / CH₂Cl₂ / 17 h / 0 °C

10: 95 percent / aq. AcOH; Zn powder / 2.5 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:

N-benzyloxycarbonyl-O--D-serine p-bromophenacyl ester

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

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

N-benzyloxycarbonyl-O-(N-t-butyloxycarbonyl-L-alanyl-S-acetamidomethyl-L-cysteinyl-L-valyl)-D-serine

Downstream raw materials:

C₄₉H₆₈N₈O₁₇S₂

(N-benzyloxycarbonyl-D-seryl-L-alanyl-L-cysteinyl-L-valine)2(serine hydroxyl)dilactone disulfide

[(3S,6R,9S,12R,16S,19R,22S,25R)-6,19-Bis-(acetylamino-methylsulfanylmethyl)-25-benzyloxycarbonylamino-3,16-diisopropyl-9,22-dimethyl-2,5,8,11,15,18,21,24-octaoxo-1,14-dioxa-4,7,10,17,20,23-hexaaza-cyclohexacos-12-yl]-carbamic acid benzyl ester