(2R,3S)-1-benzyl-3-benzyloxy-2-(tert-butyldiphenyl silyloxy)methyl-azetidine

Base Information

• Chemical Name: (2R,3S)-1-benzyl-3-benzyloxy-2-(tert-butyldiphenyl silyloxy)methyl-azetidine
• CAS No.: 150456-10-3
• Molecular Formula: C₃₄H₃₉NO₂Si
• Molecular Weight: 521.775
• Mol file: 150456-10-3.mol

Synonyms:(2R,3S)-1-benzyl-3-benzyloxy-2-(tert-butyldiphenyl silyloxy)methyl-azetidine

Chemical Property of (2R,3S)-1-benzyl-3-benzyloxy-2-(tert-butyldiphenyl silyloxy)methyl-azetidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-benzyl-3-benzyloxy-2-(tert-butyldiphenyl silyloxy)methyl-azetidine

There total 5 articles about (2R,3S)-1-benzyl-3-benzyloxy-2-(tert-butyldiphenyl silyloxy)methyl-azetidine 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: 95.0%

2-O-benzyl-4-O-tert-butyldiphenylsilyl-1,3-di-O-methylsufonyl-L-threitol (150456-09-0) + benzylamine (100-46-9) → (2R,3S)-1-benzyl-3-benzyloxy-2-(tert-butyldiphenyl silyloxy)methyl-azetidine (150456-10-3)

Guidance literature:

at 100 ℃; for 8h;

DOI:10.1016/S0040-4020(01)85738-0

Reference yield:

2-O-benzyl-L-threitol (84379-51-1,84379-52-2,124909-02-0,127000-44-6) → (2R,3S)-1-benzyl-3-benzyloxy-2-(tert-butyldiphenyl silyloxy)methyl-azetidine (150456-10-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 65 percent / CF₃COOH / CH₂Cl₂ / 15 h / Heating

2: 90 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

3: CH₃COOH, H₂O / 15 h / 40 °C

4: 92 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

5: 95 percent / 8 h / 100 °C

With 1H-imidazole; dmap; water; acetic acid; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85738-0

Reference yield:

(2S,3S)-1,3-O-Benzylidene-2-O-benzylthreitol (107938-31-8) → (2R,3S)-1-benzyl-3-benzyloxy-2-(tert-butyldiphenyl silyloxy)methyl-azetidine (150456-10-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

2: CH₃COOH, H₂O / 15 h / 40 °C

3: 92 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

4: 95 percent / 8 h / 100 °C

With 1H-imidazole; dmap; water; acetic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85738-0

upstream raw materials:

2-O-benzyl-4-O-tert-butyldiphenylsilyl-1,3-di-O-methylsufonyl-L-threitol

benzylamine

2-O-benzyl-L-threitol

(2S,3S)-1,3-O-Benzylidene-2-O-benzylthreitol

Downstream raw materials:

(2S,3S)-1-benzyl-3-benzyloxy-2-formyl-azetidine

(2R,3S)-1-benzyl-3-benzyloxy-2-hydroxymethyl-azetidine

Refernces