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

Base Information

• Chemical Name: (2R,3R)-2,3-Bis(benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-N-methoxy-N-methylbutanamide
• CAS No.: 158535-87-6
• Molecular Formula: C₂₆H₃₉NO₅Si
• Molecular Weight: 473.685
• Mol file: 158535-87-6.mol

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

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

There total 3 articles about (2R,3R)-2,3-Bis(benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-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: 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

Reference yield:

benzyl bromide (100-39-0) → (2R,3R)-2,3-Bis(benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-N-methoxy-N-methylbutanamide (158535-87-6)

Guidance literature:

Multi-step reaction with 3 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

3: 98 percent / imidazole / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; trimethylaluminum; silver(l) oxide; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00091a034

Reference yield:

(2R,3R)-2,3-bis(benzyloxy)-4-hydroxybutanoic acid 1,4-lactone (130412-79-2) → (2R,3R)-2,3-Bis(benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-N-methoxy-N-methylbutanamide (158535-87-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 98 percent / imidazole / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; trimethylaluminum; In hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00091a034

upstream raw materials:

tert-butyldimethylsilyl chloride

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

benzyl bromide

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

Downstream raw materials:

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

(+)-(SS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide

(-)-(1S,2R,8S,8aR)-1,2-di(benzyloxy)-8-methoxymethoxy-1,2,3,5,8,8a-hexahydroindolizine

(+)-(2R,3S,4R)-1-allyl-3,4-di(benzyloxy)-2-[(S)-1-(methoxymethoxy)allyl]pyrrolidine