(2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide

Base Information

• Chemical Name: (2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide
• CAS No.: 158535-86-5
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 158535-86-5.mol

Synonyms:(2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide

Chemical Property of (2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide

There total 2 articles about (2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-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:

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (2R,3R)-2,3-bis(benzyloxy)-4-hydroxybutanoic acid 1,4-lactone (130412-79-2) → (2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide (158535-86-5)

Guidance literature:

With trimethylaluminum; In hexane; dichloromethane; Yield given; 1.) r.t., 15 min, 2.) 0 deg C, 20 min;

DOI:10.1021/jo00091a034

Reference yield:

benzyl bromide (100-39-0) → (2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide (158535-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / Ag₂O / diethyl ether / 20 h / Ambient temperature

2: AlMe₃ / CH₂Cl₂; hexane / 1.) r.t., 15 min, 2.) 0 deg C, 20 min

With trimethylaluminum; silver(l) oxide; In diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo00091a034

Reference yield: 98.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide (158535-86-5) → (2R,3R)-2,3-Bis(benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-N-methoxy-N-methylbutanamide (158535-87-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1021/jo00091a034

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

(2R,3R)-2,3-bis(benzyloxy)-4-hydroxybutanoic acid 1,4-lactone

benzyl bromide

Downstream raw materials:

(2R,3R)-2,3-Bis(benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-N-methoxy-N-methylbutanamide

2,3-Di-O-benzyl-4-O-(tert-butyldimethylsilyl)-D-erythrose

(2R,3R,4R,5S,6E)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol

(2R,3R,4R,5R,6E)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol