Methyl (3R,4S)-3-benzyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hydroxypentanoate

Base Information

• Chemical Name: Methyl (3R,4S)-3-benzyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hydroxypentanoate
• CAS No.: 135505-38-3
• Molecular Formula: C₁₈H₂₇NO₅
• Molecular Weight: 337.416
• Mol file: 135505-38-3.mol

Synonyms:

Chemical Property of Methyl (3R,4S)-3-benzyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hydroxypentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (3R,4S)-3-benzyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hydroxypentanoate

There total 4 articles about Methyl (3R,4S)-3-benzyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hydroxypentanoate 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:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → Methyl (3R,4S)-3-benzyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hydroxypentanoate (135505-38-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / tetra-n-butylammonium iodide, 3 M aq. K₂CO₃ / 16 h / Ambient temperature

2: 86 percent / TMSCl / tetrahydrofuran; diethyl ether / 1.) -40 deg C, 1 h, 2.) -40 deg C to r.t. over 3 h

3: 73 percent / p-toluenesulfonic acid / toluene / 4 h / Heating

4: K₂CO₃ / methanol / Ambient temperature

5: methanol; diethyl ether

With chloro-trimethyl-silane; tetra-(n-butyl)ammonium iodide; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; toluene;

DOI:10.1021/jo00019a055

Reference yield:

(4R,5S)-5<<(1,1-Dimethylethoxy)carbonyl>amino>-4-benzyltetrahydro-2H-pyran-2-one (126587-47-1) → Methyl (3R,4S)-3-benzyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hydroxypentanoate (135505-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / methanol / Ambient temperature

2: methanol; diethyl ether

With potassium carbonate; In methanol; diethyl ether;

DOI:10.1021/jo00019a055

Reference yield:

(4S,1'RS)-1,1-Dimethylethyl 4-<3'-methoxy-3'-oxo-1'-benzylpropyl>-2,2-dimethyl-3-oxazolidinecarboxylate (129483-74-5,129483-79-0) → Methyl (3R,4S)-3-benzyl-4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hydroxypentanoate (135505-38-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / p-toluenesulfonic acid / toluene / 4 h / Heating

2: K₂CO₃ / methanol / Ambient temperature

3: methanol; diethyl ether

With potassium carbonate; toluene-4-sulfonic acid; In methanol; diethyl ether; toluene;

DOI:10.1021/jo00019a055

upstream raw materials:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(4R,5S)-5<<(1,1-Dimethylethoxy)carbonyl>amino>-4-benzyltetrahydro-2H-pyran-2-one

(4S,1'RS)-1,1-Dimethylethyl 4-<3'-methoxy-3'-oxo-1'-benzylpropyl>-2,2-dimethyl-3-oxazolidinecarboxylate

(4S)-1,1-Dimethylethyl 4-(3'-methoxy-3'-oxo-1'-propenyl)-2,2-dimethyl-3-oxazolidinecarboxylate

Downstream raw materials:

(2S,3R)-2-Amino-3-benzyl-1,5-pentanedioic acid hydrochloride

Dimethyl (2S,3R)-3-benzyl-2-<<(1,1-dimethylethoxy)carbonyl>amino>-1,5-pentanedioate

Refernces