(R)-2-((2S,3S)-3-((R)-1-((tert-Butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)propanoic acid

Base Information

• Chemical Name: (R)-2-((2S,3S)-3-((R)-1-((tert-Butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)propanoic acid
• CAS No.: 90776-58-2
• Molecular Formula: C₁₄H₂₇NO₄Si
• Molecular Weight: 301.458
• European Community (EC) Number: 618-645-7
• DSSTox Substance ID: DTXSID90432351
• Nikkaji Number: J392.367C
• Wikidata: Q72507496
• Mol file: 90776-58-2.mol

Synonyms:90776-58-2;(R)-2-((2S,3S)-3-((R)-1-((tert-Butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)propanoic acid;4-bma;side chain for imipenem;(3s,4s)-4-[(r)-1-carboxyethyl]-3-[(r)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone;(r)-2-[(3s,4s)-3-[(r)-1-(tert-butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid;93711-85-4;(3S,4S)-3-((R)-(tert-Butyldimethyl-silyloxy)ethyl)-4((R)-carboxyethyl)-2-azetidinone;(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-4-[(R)-1-carboxyethyl]-2-azetidinone;(3s 4s)-3-[ (r)-1-(t-butyldimethylsilyloxy)ethyl]-4[(r)-1-carboxyethyl]-2-azetidinone;(r)-2-((2s,3s)-3-((r)-1-(tert-butyldimethylsilyloxy)ethyl)-4-oxoazetidin-2-yl)propanoic acid;(2R)-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanoic acid;(3S,4S)-3-[(R)-Butyldimethylsilyloxy)ethyl]-4-[(R)-carboxyethyl]-2-azetidinone;C14H27NO4Si;MFCD00272297;4bma;(R)-2-[(2S,3S)-3-[(R)-1-[(tert-Butyldimethylsilyl)oxy]ethyl]-4-oxo-2-azetidinyl]propanoic Acid;SCHEMBL2328228;Butyldimethylsilyloxyethylcarboxyet;DTXSID90432351;NNANGMFTFSNDLW-GWOFURMSSA-N;BCP13009;AC8216;AKOS015836361;AKOS015950795;AC-4274;AS-14337;2,2-(ETHYLENEDIIMINO)-DIBUTYRICACID;CS-0170833;A916447;Q-101432;(3S ,4S)-3-[(1R)-1-t-Butyldimethylsilyloxyethyl]-4-[(1R)-1-carboxyethyl]-2-azetidinone;(3s 4s)-3-[(r)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(r)-1-carboxyethyl]-2-azetidinone;(3s,4s)-3-((r)-(t-butyldimethyl silyloxy)ethyl)-4-((r)-carboxy ethyl)-2-azetidinone;(3s,4s)-3-((r)-(tert-butyldimethyl-silyloxy)ethyl)-4-((r)-carboxyethyl)-2-azetidinone;(3s,4s)-3-[((r)-butyldimethylsilyloxy)ethyl]-4-[(r)-carboxyethyl]-2-azetidinone;(3S,4S)-3-[(1R)-1-t-Butyldimethylsilyloxyethyl]-4-[(1R)-1-carboxyethyl]-2-azetidinone;(3s,4s)-3-[(r)-(butyldimethylsilyloxy)ethyl]-4-[(r)-carboxyethyl]-2-azetidinone;(3s,4s)-3-[(r)-1-(tert-butyldimethylsiloxy)ethyl]-4-[(r)-1-carboxyethyl]-2-azetidinone;(3S,4S)-3-[(R)-Butyldimethylsilyloxy)ethyl]-4-[(R)-carboxyethyl]-2azetidinone;(3s,4s)-4-(r)-1-carboxyethyl-3-(r)-1-(t-butyldimethylsilyloxy)ethyl-2-azetidinone;3alpha-[(R)-1-(tert-Butyldimethylsiloxy)ethyl]-4beta-[(R)-1-carboxyethyl]azetidin-2-one;(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid;(2R)-2-{(2S,3S)-3-[(1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}ethyl]-4-oxoazetidin-2-yl}propanoic acid;(3s,4s)-3-[(r)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(r)- 1-carboxyethyl]-2-azetidinone;(ar,2s,3s)-3-[(1r)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-a-methyl-4-oxo-2-azetidineacetic;(R)-2-((2S,3S)-3-((R)-1-((tert-Butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)propanoicacid;(r)-2-[(3s,4s)-3-[(r)-1-(tert-butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionicacid;(R)-2-[(3S,4S)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionic acid;(R)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl--silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid

Chemical Property of (R)-2-((2S,3S)-3-((R)-1-((tert-Butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)propanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 146-147 °C
• Refractive Index: 1.471
• Boiling Point: 424.392 °C at 760 mmHg
• PKA: 4.22±0.10(Predicted)
• Flash Point: 210.465 °C
• PSA: 75.63000
• Density: 1.05 g/cm³
• LogP: 2.56080
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 301.17093488
• Heavy Atom Count: 20
• Complexity: 403

Purity/Quality:

98% ^*data from raw suppliers

(3S,4S)-4-[(R)-1-carboxyethyl]-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C(NC1=O)C(C)C(=O)O)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: C[C@H]([C@@H]1[C@H](NC1=O)[C@@H](C)C(=O)O)O[Si](C)(C)C(C)(C)C
• Uses: Harmful by inhalation and in contact with skin

Technology Process of (R)-2-((2S,3S)-3-((R)-1-((tert-Butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)propanoic acid

There total 144 articles about (R)-2-((2S,3S)-3-((R)-1-((tert-Butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)propanoic acid 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:

(4S,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(4S,5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

1-α-methyl RS-533

(4R,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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.