(3R,4S,5R)-2-Benzyl-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-methyl-isoxazolidine-4-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3R,4S,5R)-2-Benzyl-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-methyl-isoxazolidine-4-carboxylic acid benzyl ester
• CAS No.: 112057-65-5
• Molecular Formula: C₂₈H₄₁NO₄Si
• Molecular Weight: 483.723
• Mol file: 112057-65-5.mol

Synonyms:(3R,4S,5R)-2-Benzyl-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-methyl-isoxazolidine-4-carboxylic acid benzyl ester

Chemical Property of (3R,4S,5R)-2-Benzyl-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-methyl-isoxazolidine-4-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-2-Benzyl-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-methyl-isoxazolidine-4-carboxylic acid benzyl ester

There total 5 articles about (3R,4S,5R)-2-Benzyl-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-methyl-isoxazolidine-4-carboxylic acid benzyl ester 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:

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester (93454-85-4) → (3R,4S,5R)-2-Benzyl-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-methyl-isoxazolidine-4-carboxylic acid benzyl ester (112057-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.08 h / -78 °C

2: 64 percent / 1.) CaCl₂ / diethyl ether / 1.) 0 deg C, 1 h; 2.) r.t., 2 h

3: toluene / 24 h / 80 °C

With diisobutylaluminium hydride; calcium chloride; In diethyl ether; hexane; toluene;

DOI:10.1246/bcsj.60.3337

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3R,4S,5R)-2-Benzyl-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-methyl-isoxazolidine-4-carboxylic acid benzyl ester (112057-65-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

2: 78 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.08 h / -78 °C

3: 64 percent / 1.) CaCl₂ / diethyl ether / 1.) 0 deg C, 1 h; 2.) r.t., 2 h

4: toluene / 24 h / 80 °C

With 1H-imidazole; diisobutylaluminium hydride; calcium chloride; In diethyl ether; hexane; N,N-dimethyl-formamide; toluene;

DOI:10.1246/bcsj.60.3337

Reference yield:

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal (104701-87-3) → (3R,4S,5R)-2-Benzyl-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5-methyl-isoxazolidine-4-carboxylic acid benzyl ester (112057-65-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / 1.) CaCl₂ / diethyl ether / 1.) 0 deg C, 1 h; 2.) r.t., 2 h

2: toluene / 24 h / 80 °C

With calcium chloride; In diethyl ether; toluene;

DOI:10.1246/bcsj.60.3337

upstream raw materials:

benzyl (E)-2-butenoate

(R)-(-)-N-(3-t-butyldimethylsilyloxy-2-methylpropylidene)benzylamine N-oxide

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester

Downstream raw materials:

(3R,4S,5R)-3-((R)-2-Acetoxy-1-methyl-ethyl)-2-benzyl-5-methyl-isoxazolidine-4-carboxylic acid benzyl ester