(2S,3R,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate

Base Information

• Chemical Name: (2S,3R,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate
• CAS No.: 1435460-77-7
• Molecular Formula: C₂₇H₂₉NO₄
• Molecular Weight: 431.532
• Mol file: 1435460-77-7.mol

Synonyms:

Chemical Property of (2S,3R,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate

There total 4 articles about (2S,3R,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate 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:

(S,Z)-methyl 2-benzamido-7-oxo-3,5-diphenylhept-2-enoate (1435460-73-3) → (2R,3S,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate (1435460-75-5) + (2S,3R,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate (1435460-77-7)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; for 10h; under 15001.5 Torr; Overall yield = 99 %; Overall yield = 172.5 mg;

DOI:10.1021/ja4029928

Reference yield:

2-phenyl-4-(1-phenylethylidene)oxazol-5(4H)-one (68099-99-0) → (2R,3S,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate (1435460-75-5) + (2S,3R,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate (1435460-77-7)

Guidance literature:

Multi-step reaction with 3 steps

1: (S)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine; triethylamine; sodium chloride / dichloromethane; water / 20 h / 20 °C

2: potassium carbonate / 20 °C / Inert atmosphere

3: palladium on activated charcoal; hydrogen / ethyl acetate / 10 h / 20 °C / 15001.5 Torr

With (S)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine; palladium on activated charcoal; hydrogen; potassium carbonate; triethylamine; sodium chloride; In dichloromethane; water; ethyl acetate; 1: |Michael Addition;

DOI:10.1021/ja4029928

Reference yield:

(S,Z)-5-(5-oxo-2-phenyloxazol-4(5H)-ylidene)-3,5-diphenylpentanal (1435459-58-7) → (2R,3S,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate (1435460-75-5) + (2S,3R,5S)-methyl 2-benzamido-7-hydroxy-3,5-diphenylheptanoate (1435460-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / 20 °C / Inert atmosphere

2: palladium on activated charcoal; hydrogen / ethyl acetate / 10 h / 20 °C / 15001.5 Torr

With palladium on activated charcoal; hydrogen; potassium carbonate; In ethyl acetate;

DOI:10.1021/ja4029928

upstream raw materials:

(S,Z)-5-(5-oxo-2-phenyloxazol-4(5H)-ylidene)-3,5-diphenylpentanal

(S,Z)-methyl 2-benzamido-7-oxo-3,5-diphenylhept-2-enoate

2-phenyl-4-(1-phenylethylidene)oxazol-5(4H)-one

3-phenyl-propenal