(4S)-4-<(1R)-1-(benzyloxycarbonyl)ethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine

Base Information

• Chemical Name: (4S)-4-<(1R)-1-(benzyloxycarbonyl)ethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine
• CAS No.: 102832-01-9
• Molecular Formula: C₁₉H₂₉NO₃Si
• Molecular Weight: 347.53
• Mol file: 102832-01-9.mol

Synonyms:(4S)-4-<(1R)-1-(benzyloxycarbonyl)ethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine

Chemical Property of (4S)-4-<(1R)-1-(benzyloxycarbonyl)ethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-<(1R)-1-(benzyloxycarbonyl)ethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine

There total 4 articles about (4S)-4-<(1R)-1-(benzyloxycarbonyl)ethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine 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: 40.0%

(4S)-1-(tert-Butyldimethylsilyl)-4-<(1R)-1-<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one (102831-99-2) + sodium phenyl-methanolate (20194-18-7) → (4S)-4-<(1R)-1-(benzyloxycarbonyl)ethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine (102832-01-9)

Guidance literature:

In toluene; 0 deg C, 1 h, than rt., 30 min;

DOI:10.1021/ja00275a082

Reference yield:

(4S)-4-<(1R)-1-<((4S)-4-Ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one (102831-94-7) → (4S)-4-<(1R)-1-(benzyloxycarbonyl)ethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine (102832-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Et₃N / dimethylformamide / 0 °C

2: 40 percent / toluene / 0 deg C, 1 h, than rt., 30 min

With triethylamine; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00275a082

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (4S)-4-<(1R)-1-(benzyloxycarbonyl)ethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine (102832-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Et₃N / dimethylformamide / 0 °C

2: 40 percent / toluene / 0 deg C, 1 h, than rt., 30 min

With triethylamine; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00275a082

upstream raw materials:

(4S)-1-(tert-Butyldimethylsilyl)-4-<(1R)-1-<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one

sodium phenyl-methanolate

3-[(2R)-2-((4S)-1-tert-butyldimethylsilyl-2-oxoazetidin-4-yl)propionyl]-spiro[2,3-dihydro-4H-1,3-benzoxazin-2,1'-((2'R,5'S)-2'-isopropyl-5'-methylcyclohexane)]-4-one

benzyl alcohol

Downstream raw materials:

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one

(3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one