ethyl O-benzyl-α-(α-hydroxyisovaleryl)propionate

Base Information

• Chemical Name: ethyl O-benzyl-α-(α-hydroxyisovaleryl)propionate
• CAS No.: 110720-20-2
• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.375
• Mol file: 110720-20-2.mol

Synonyms:

Chemical Property of ethyl O-benzyl-α-(α-hydroxyisovaleryl)propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl O-benzyl-α-(α-hydroxyisovaleryl)propionate

There total 1 articles about ethyl O-benzyl-α-(α-hydroxyisovaleryl)propionate 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:

monoethyl methylmalonate (2985-33-3) + (2S)-2-(benzyloxy)-3-methylbutanoyl chloride (110720-19-9) → ethyl O-benzyl-α-(α-hydroxyisovaleryl)propionate (110720-20-2,110720-21-3)

Guidance literature:

With magnesium; Multistep reaction;

DOI:10.1021/ja00256a046

Reference yield:

ethyl O-benzyl-α-(α-hydroxyisovaleryl)propionate (110720-20-2,110720-21-3) → didemnin B (77327-05-0,114607-50-0,128821-14-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 0.5N potassium hydroxide

2: 71 percent / HOBt, DCC / 0 °C

3: H₂ / 10percent Pd/C / propan-2-ol

4: 76 percent / DMAP, DCC / 0 °C

5: 90 percent / Bu₄N⁽¹⁺⁾*F^(1-) / Ambient temperature

6: 40 percent / HOBt, EDC / 0 °C

7: 95 percent / Bu₄N⁽¹⁺⁾*F^(1-) / Ambient temperature

8: 99 percent / TFA-OH / 0 °C

9: 18 percent / NMM, HOBt, EDC / Ambient temperature

10: 88 percent / H₂ / 10percent Pd/C

12: H₂ / Pd/C

With 4-methyl-morpholine; dmap; potassium hydroxide; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In isopropyl alcohol;

DOI:10.1021/ja00256a046

Reference yield:

ethyl O-benzyl-α-(α-hydroxyisovaleryl)propionate (110720-20-2,110720-21-3) → didemnin A (77327-04-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 0.5N potassium hydroxide

2: 71 percent / HOBt, DCC / 0 °C

3: H₂ / 10percent Pd/C / propan-2-ol

4: 76 percent / DMAP, DCC / 0 °C

5: 90 percent / Bu₄N⁽¹⁺⁾*F^(1-) / Ambient temperature

6: 40 percent / HOBt, EDC / 0 °C

7: 95 percent / Bu₄N⁽¹⁺⁾*F^(1-) / Ambient temperature

8: 99 percent / TFA-OH / 0 °C

9: 18 percent / NMM, HOBt, EDC / Ambient temperature

10: 88 percent / H₂ / 10percent Pd/C

With 4-methyl-morpholine; dmap; potassium hydroxide; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In isopropyl alcohol;

DOI:10.1021/ja00256a046

upstream raw materials:

monoethyl methylmalonate

(2S)-2-(benzyloxy)-3-methylbutanoyl chloride

Downstream raw materials:

Bzl-Hip-OH

Z-D-MeLeu-Thr(OTMSe)-O-Me₂Tyr-Pro-Leu-Hip-Ist-Boc

Z-D-MeLeu-Thr(OTMSe)-O-Me₂Tyr-Pro-Leu-Hip-Sta-Boc

Bzl-Hip-Leu-OTMSe