N-Cbz-(D)-Ala-(L)-Leu-O-tBu

Base Information

• Chemical Name: N-Cbz-(D)-Ala-(L)-Leu-O-tBu
• CAS No.: 78031-81-9
• Molecular Formula: C₂₁H₃₂N₂O₅
• Molecular Weight: 392.495
• Mol file: 78031-81-9.mol

Synonyms:N-Cbz-(D)-Ala-(L)-Leu-O-tBu

Chemical Property of N-Cbz-(D)-Ala-(L)-Leu-O-tBu

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Cbz-(D)-Ala-(L)-Leu-O-tBu

There total 2 articles about N-Cbz-(D)-Ala-(L)-Leu-O-tBu 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:

L-leucine tert-butyl ester (21691-53-2) + N-benzyloxycarbonyl-D-alanine (26607-51-2) → N-Cbz-(D)-Ala-(L)-Leu-O-tBu (78031-81-9)

Guidance literature:

With diethyl cyanophosphonate; TEA; In N,N-dimethyl-formamide;

Reference yield:

→ N-Cbz-(D)-Ala-(L)-Leu-O-tBu (78031-81-9)

Guidance literature:

Z-D-Ala, L-Leu-OtBu, Ether;

Reference yield:

N-Cbz-(D)-Ala-(L)-Leu-O-tBu (78031-81-9) → Microcystin-LA (96180-79-9)

Guidance literature:

Multi-step reaction with 15 steps

1: H₂ / 10percent Pd/C / methanol / 2.5 h / 760 Torr

2: HOBt, DCC / CH₂Cl₂ / a) 0 deg C, 2 h, b) RT, 12 h

3: H₂ / 10percent Pd/C / methanol / 2.5 h / 760 Torr

4: DIEA, HATU / dimethylformamide / a) 0 deg C, 1 h, b) RT, 17 h

5: aq. K₂CO₃ / tetrahydrofuran / 8 h / Ambient temperature

6: TFA, thioanisole / 0.5 h

7: aq. Na₂CO₃ / dioxane / 12 h / Ambient temperature

8: collidine, HATU / dimethylformamide / a) 0 deg C, 1 h, b) RT, 19 h

9: TFA / 0.5 h

10: collidine, HATU / dimethylformamide / a) 0 deg C, 1 h, b) RT, 14 h

11: 84 percent / Zn, HOAc / 4 h

12: 83 percent / DCC / ethyl acetate / a) 0 deg C, 2 h, b) RT, 22 h

13: TFA / 0.83 h

14: phosphate buffer, pH 9.5 / CHCl₃ / 1 h

15: 50 percent / 0.1 M aq. LiOH / tetrahydrofuran / 5 h / 0 °C

With 2,3,5-trimethyl-pyridine; lithium hydroxide; phosphate buffer; methyl-phenyl-thioether; hydrogen; sodium carbonate; potassium carbonate; benzotriazol-1-ol; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja961683e

upstream raw materials:

L-leucine tert-butyl ester

N-benzyloxycarbonyl-D-alanine

Downstream raw materials:

Cbz-N-(Me)-Gly-D-Ala-L-Leu-OtBu

Cbz-N-(cyclohexyl)-Gly-D-Ala-L-leu-OtBu

Boc-D-iso-Glu(OMe)-N-(cyclohexyl)-Gly-D-Ala-L-Leu-OH

Boc-D-iso-Glu(OMe)-N-(cyclohexyl)-Gly-D-Ala-L-Leu-OtBu