(2R,3R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-oxoazetidin-2-yl acetate

• ChemBase ID: 149303
• Molecular Formular: C13H25NO4Si
• Molecular Mass: 287.4274
• Monoisotopic Mass: 287.15528482
• SMILES: C[C@H]([C@@H]1[C@H](NC1=O)OC(=O)C)O[Si](C)(C)C(C)(C)C
• Canonical SMILES: CC(=O)O[C@H]1NC(=O)[C@@H]1[C@H](O[Si](C(C)(C)C)(C)C)C
• InChI: InChI=1S/C13H25NO4Si/c1-8(18-19(6,7)13(3,4)5)10-11(16)14-12(10)17-9(2)15/h8,10,12H,1-7H3,(H,14,16)/t8-,10+,12-/m1/s1
• InChIKey: GWHDKFODLYVMQG-UBHAPETDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-oxoazetidin-2-yl acetate
• IUPAC Traditional name: (2R,3R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-oxoazetidin-2-yl acetate
• Synonyms: [3R-[3α(R*),4β]]-4-(Acetyloxy)-3-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-2-azetidinone; (1'R,3R,4R)-4-Acetoxy-3-(1'-tert-butyldimethylsilyloxyethyl)-2-azetidinone; (3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]azetidin-2-one; (3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidinone; (3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone; [3R(1′R,4R)]-(+)-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone; [3R(1′R,4R)]-(+)-4-乙酰氧基-3-[1-(叔丁基二甲基硅氧基)乙基]-2-氮杂环丁酮

Database IDs

• CAS Number: 76855-69-1
• EC Number: 408-050-9
• MDL Number: MFCD00077636
• PubChem SID: 24863408; 162243471
• PubChem CID: 10935078

CALCULATED PROPERTIES

• Acid pKa: 10.6731825
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.6648973
• LogD (pH = 7.4): 1.6646852
• Log P: 1.6649
• Molar Refractivity: 68.3004 cm^3
• Polarizability: 29.597801 Å^3
• Polar Surface Area: 64.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 107-109 °C(lit.); 108-110°C
• Optical Rotation: [α]20/D +51°, c = 1 in chloroform

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36-43-51/53
• Safety Statements: 24-26-37-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319-H411
• GHS Precautionary statements: P273-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C13H25NO4Si

DETAILS

Sigma Aldrich - 375845

Packaging
1 g in glass bottle

Toronto Research Chemicals - A164500

An acetoxyazetidinone derivative used as an intermediate in the preparation of carbapenem antibiotics.