(3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one

Base Information

• Chemical Name: (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one
• CAS No.: 97101-07-0
• Molecular Formula: C₁₄H₂₇NO₄Si
• Molecular Weight: 301.458
• Mol file: 97101-07-0.mol

Synonyms:(3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one

Chemical Property of (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one

Chemical Property:

• Boiling Point: 424.4±10.0 °C(Predicted)
• Density: 1.050±0.06 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one

There total 153 articles about (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>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: 98.0%

(3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone (96035-98-2) → (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid (93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 4h;

DOI:10.1016/S0040-4020(01)87086-1

Reference yield: 94.1%

4-acetoxy azetidinone (28562-53-0) + 3-(2-chloro-1-oxopropyl)spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one (1332594-11-2) → (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid (93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2)

Guidance literature:

4-acetoxy azetidinone; With zinc; In tetrahydrofuran; at 60 ℃; for 1h;

3-(2-chloro-1-oxopropyl)spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one; at 40 ℃; for 4h;

Reference yield: 92.0%

3-<(2R)-2-<(2R,3S)-3-<(1R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-oxoazetidin-2-yl>propionyl>spiro-<2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan>-4-one (158299-15-1) → (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid (93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2)

Guidance literature:

With dihydrogen peroxide; sodium hydrogencarbonate; In water; at 5 - 10 ℃; for 2h; pH=8; Reagent/catalyst;

upstream raw materials:

N-isopropyl oxazolidinone

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

2-[(E)-1-(tert-Butyl-dimethyl-silanyloxy)-propenylsulfanylmethyl]-3-methyl-pyridine

methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionate

Downstream raw materials:

(3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-2-oxo-propyl]-azetidin-2-one

S-[(2R,3R)-tetrahydro-2-[[[(S)-3-methyl-2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-1-oxobutyl]amino]methyl]-3-furanyl](α,2S,3S)-3-[(R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-α-methyl-4-oxo-2-azetidinemethanethiolate

(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-1-[[(p-nitrobenzyl)oxy]oxalyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone