(3S,1'R)-N-(1'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>-4-carbomethoxybutanamide

Base Information

• Chemical Name: (3S,1'R)-N-(1'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>-4-carbomethoxybutanamide
• CAS No.: 91424-38-3
• Molecular Formula: C₂₀H₃₃NO₄Si
• Molecular Weight: 379.572
• Mol file: 91424-38-3.mol

Synonyms:

Chemical Property of (3S,1'R)-N-(1'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>-4-carbomethoxybutanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,1'R)-N-(1'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>-4-carbomethoxybutanamide

There total 3 articles about (3S,1'R)-N-(1'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>-4-carbomethoxybutanamide 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-hydroxypentanedioic acid monomethyl ester (87118-53-4) → (3S,1'R)-N-(1'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>-4-carbomethoxybutanamide (91424-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / CH₂Cl₂ / 24 h / Ambient temperature

2: 1) oxalyl chloride / DMF / CH₂Cl₂, 1) 1.5h at 0 deg C; 25 min at r.t. 2) 0 deg C; 2h at r.t.

With 1H-imidazole; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1021/jo00193a044

Reference yield:

(R)-1-phenyl-ethyl-amine (3886-69-9) → (3S,1'R)-N-(1'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>-4-carbomethoxybutanamide (91424-38-3) + (3R,1'R)-N-(1'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>-4-carbomethoxybutanamide (91424-37-2)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; Multistep reaction; CH₂Cl₂, 1) 0 deg C to r.t. 2) 0 deg C to r.t.;

DOI:10.1021/jo00193a044

Reference yield:

(R)-1-phenyl-ethyl-amine (3886-69-9) + (S)-methyl tert-butyldimethylsilyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate (91424-35-0) → (3S,1'R)-N-(1'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>-4-carbomethoxybutanamide (91424-38-3) + (3R,1'R)-N-(1'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>-4-carbomethoxybutanamide (91424-37-2)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; Multistep reaction; CH₂Cl₂, 1) 1.5h at 0 deg C; 25 min at r.t. 2) 0 deg C; 2h at r.t.;

DOI:10.1021/jo00193a044

upstream raw materials:

(R)-1-phenyl-ethyl-amine

(S)-methyl tert-butyldimethylsilyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate

(R)-3-hydroxypentanedioic acid monomethyl ester

Refernces