(2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide

Base Information

• Chemical Name: (2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide
• CAS No.: 871514-35-1
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• Mol file: 871514-35-1.mol

Synonyms:(2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide

Chemical Property of (2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide

There total 2 articles about (2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide 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: 92.0%

(4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbonyl chloride + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide (871514-35-1)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2005.09.030

Reference yield:

(2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butyric acid (871514-34-0) → (2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide (871514-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; DMF / CH₂Cl₂ / 0.5 h / 20 °C

2: 92 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1016/j.tet.2005.09.030

Reference yield: 85.0%

(2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide (871514-35-1) + ethyl vinyl ether (109-92-2,25104-37-4) → (4R,5S)-6-benzyloxy-4,5-(dimethylmethylenedioxy)-2-ethoxy-1-hexen-3-one (871514-36-2)

Guidance literature:

ethyl vinyl ether; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - 0 ℃; for 0.5h;

(2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide; In tetrahydrofuran; pentane; at -78 ℃; for 3h;

DOI:10.1016/j.tet.2005.09.030

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

(2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butyric acid

Downstream raw materials:

(4R,5S)-6-benzyloxy-4,5-(dimethylmethylenedioxy)-2-ethoxy-1-hexen-3-one

ethyl (3R,4S)-5-benzyloxy-4,5-(dimethylmethylenedioxy)-2-oxopentanoate

ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(dimethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(dimethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate