(3S,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one
• CAS No.: 122797-12-0
• Molecular Formula: C₂₃H₃₁NO₃Si
• Molecular Weight: 397.59
• Mol file: 122797-12-0.mol

Synonyms:(3S,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one

Chemical Property of (3S,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one

There total 6 articles about (3S,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one 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: 19.0%

(S)-3-Amino-5-(tert-butyl-diphenyl-silanyloxy)-2-((S)-1-hydroxy-ethyl)-pentanoic acid methyl ester (122717-05-9,122797-09-5,122797-15-3,122797-16-4) → (3S,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one (122717-07-1) + (3S,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one (122797-12-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)72728-6

Reference yield: 14.0%

(S)-3-Amino-5-(tert-butyl-diphenyl-silanyloxy)-2-((S)-1-hydroxy-ethyl)-pentanoic acid isopropyl ester (122717-06-0,122797-10-8,122797-17-5,122797-18-6) → (3S,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one (122717-07-1) + (3S,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one (122797-12-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)72728-6

Reference yield:

[3-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-propyl]-carbamic acid tert-butyl ester (122716-72-7) → (3S,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-((S)-1-hydroxy-ethyl)-azetidin-2-one (122797-12-0)

Guidance literature:

Multi-step reaction with 3 steps

1: LDA / tetrahydrofuran / 2 h / -70 gradC to 0 gradC

2: TFA / 0.5 h / 0 °C

3: 19 percent / LDA / tetrahydrofuran / 2 h / 0 °C

With trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)72728-6

upstream raw materials:

(S)-3-Amino-5-(tert-butyl-diphenyl-silanyloxy)-2-((S)-1-hydroxy-ethyl)-pentanoic acid methyl ester

(S)-3-Amino-5-(tert-butyl-diphenyl-silanyloxy)-2-((S)-1-hydroxy-ethyl)-pentanoic acid isopropyl ester

[3-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-propyl]-carbamic acid tert-butyl ester

tert-butylchlorodiphenylsilane

Downstream raw materials:

(3S,4R)-4-(2-hydroxyethyl)-3-[(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-oxoazetidine