(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone

Base Information

• Chemical Name: (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone
• CAS No.: 93711-85-4
• Molecular Formula: C₁₄H₂₇NO₄Si
• Molecular Weight: 301.458
• Mol file: 93711-85-4.mol

Synonyms:

Chemical Property of (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone

Chemical Property:

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

Purity/Quality:

99% ^*data from raw suppliers

(R)-2-[(3S,4s)-3-[(r)-1-(tert-butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone

There total 144 articles about (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone 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

(γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester

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

Refernces

• 1、 -. "Preparation method of meropenem intermediate 4-BMA". Paragraph 0085; 0086; 0087; 0088; 0089; 0090; 0091-0123. . Retrieved 2017/03/18.
• 2、 -. "Method for manufacturing stereoselective preparation of 4-bma using a chiral auxiliary and chiral auxiliary". Page/Page column 5; 9. . Retrieved 2011/08/04.