[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate

C13H25NO4Si

CAS76855-69-1
GHS07 Gefahrensymbol: Gesundheitsschädlich/Reizend – Ausrufezeichen
GHS09 Gefahrensymbol: Umweltgefährlich – Umwelt
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Identification

CAS Number
76855-69-1
EC Number
408-050-9
UN Number
3077
Index Number
613-186-00-9
PubChem CID
10935078

Physical-chemical properties

Molecular Formula
C13H25NO4Si
Molar Mass
287.43 g/mol
IUPAC Name
[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate

Chemical Identifiers

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
InChI Key
GWHDKFODLYVMQG-UBHAPETDSA-N

Overview

[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate (CAS 76855-69-1) is a specialized silyl-protected azetidinone derivative featuring controlled stereochemistry for pharmaceutical synthesis applications. This organosilicon compound represents an important class of protected β-lactam intermediates used in synthetic organic chemistry. The molecule combines a four-membered azetidinone ring with a tert-butyldimethylsilyl (TBDMS) protecting group, providing both structural stability and selective reactivity patterns essential for complex pharmaceutical manufacturing processes. The specific stereochemical configuration (2R,3R,1R) ensures precise molecular orientation critical for downstream synthetic transformations. The compound exhibits moderate hazard characteristics, classified as Eye Irritant Category 2 and Skin Sensitizer Category 1, requiring appropriate handling protocols including protective eyewear and gloves. Its environmental classification as Aquatic Chronic Category 2 necessitates controlled disposal methods. Transport classification under ADR Class 9 (miscellaneous dangerous substances) reflects its specialized chemical nature without immediate acute toxicity concerns. Primary industrial applications include pharmaceutical intermediate synthesis, particularly in antibiotic development where controlled β-lactam chemistry is essential. The silyl protection strategy allows for selective deprotection under mild acidic conditions, making it valuable in multi-step synthetic sequences. Advanced organic synthesis laboratories utilize this compound alongside related protective reagents such as triphenyl phosphite for complex molecule construction. The compound's utility extends to research applications in medicinal chemistry, where the combination of stereochemical control and protective group chemistry enables sophisticated molecular modifications. Its role in developing novel β-lactam-based therapeutics continues to drive demand in specialized pharmaceutical manufacturing. OYSI provides this high-purity specialty chemical to qualified pharmaceutical and research customers across European markets.

Safety & Classification

Warning
Classification:

Eye Irrit. 2; Skin Sens. 1; Aquatic Chronic 2

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H319

Causes serious eye irritation.

H317

May cause an allergic skin reaction.

H411

Toxic to aquatic life with long lasting effects.

Classification according to CLP Regulation (EC) No 1272/2008. The complete list of hazard and precautionary statements can be found in the Safety Data Sheet (SDS).

First Aid Measures

Skin Contact

Irritant

Measures if substance contacts the skin

First Aid Actions

  • +P302IF ON SKIN:
  • +P352Wash with plenty of water.
  • +P361Take off immediately all contaminated clothing.
  • +P313Get medical advice/attention.

Related hazard statements:

Eye Contact

Irritant

Measures if substance gets into the eyes

First Aid Actions

  • +P305IF IN EYES:
  • +P351Rinse cautiously with water for several minutes.
  • +P338Remove contact lenses, if present and easy to do. Continue rinsing.
  • +P313Get medical advice/attention.

Related hazard statements:

General Measures

Emergency 112 | Poison Control: +49 30 19240 (DE), +33 1 45 42 59 59 (FR), +31 30 274 88 88 (NL)

First aid measures are based on CLP classification and associated P-statements. They do not replace the Safety Data Sheet (SDS). In case of emergency, always consult the full SDS and a physician.

Transport (ADR)

UN Number3077
ADR Class9
Packing GroupIII
Tunnel Code-
Proper Shipping Name(2R,3R)-3-((R)-1-(tert-Butyldimethylsiloxy)ethyl)-4-oxoazetidin-2-ylacetat
Marine PollutantNo

Frequently Asked Questions

What is [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate?

[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate is a synthetic organic compound with the molecular formula C13H25NO4Si and CAS number 76855-69-1. This azetidinone derivative has a molecular weight of 287.43 g/mol and features a four-membered β-lactam ring protected with tert-butyldimethylsilyl and acetate groups. The compound is classified as an eye irritant and skin sensitizer under GHS regulations.

What are the physicochemical properties of [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate?

[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate is an organosilicon compound with a molecular weight of 287.43 g/mol. As a silyl-protected β-lactam derivative, it typically exists as a solid or viscous liquid at room temperature. The presence of both hydrophobic silyl groups and polar ester functionalities suggests moderate solubility in organic solvents. Specific physical properties should be confirmed through technical documentation.

What is [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate used for?

[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate is primarily used as an intermediate in pharmaceutical synthesis and organic chemistry research. Its β-lactam structure and protective groups make it valuable for developing β-lactam antibiotics and related compounds. The stereospecific configuration (2R,3R,1R) suggests applications in asymmetric synthesis and as a building block for complex pharmaceutical molecules requiring precise stereochemistry.

How to handle [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate safely?

[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate requires careful handling due to its eye irritation and skin sensitization properties. Always wear safety goggles, chemical-resistant gloves, and protective clothing when handling. Work in well-ventilated areas or under fume hoods to minimize inhalation exposure. Avoid direct skin and eye contact, and wash hands thoroughly after use. Follow standard laboratory safety protocols for handling sensitizing chemicals.

How to store [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate correctly?

[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate should be stored in tightly sealed containers away from light, heat, and moisture. Keep in a cool, dry place with temperatures below 25°C to prevent degradation of the silyl protecting groups. Store away from strong acids, bases, and oxidizing agents. Ensure adequate ventilation in storage areas and maintain proper labeling with hazard warnings for eye irritation and skin sensitization.

What to do in case of contact with [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate?

Eye contact with [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate requires immediate flushing with clean water for at least 15 minutes and seeking medical attention. For skin contact, remove contaminated clothing and wash thoroughly with soap and water due to sensitization risk. If inhaled, move to fresh air immediately. In case of ingestion, rinse mouth and seek medical advice. Always have safety data sheets readily available for emergency responders.

How to dispose of [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate appropriately?

[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate must be disposed of according to local and national hazardous waste regulations. As a potentially harmful chemical to aquatic environments (Aquatic Chronic 2), it cannot be disposed of down drains or in regular waste. Contact licensed hazardous waste disposal companies for proper treatment. Small laboratory quantities may be suitable for high-temperature incineration at authorized facilities.

How to transport [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate?

[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate is classified as ADR Class 9 (miscellaneous dangerous goods), Packing Group III. Transport requires appropriate UN-specification packaging and proper dangerous goods documentation. Packages must display correct hazard labels and shipping names. Ensure carriers are trained in dangerous goods transport and follow ADR regulations for Class 9 substances during road transport within Europe.

Is [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate subject to specific regulations?

[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate is subject to REACH regulation in Europe and must comply with CLP classification requirements. It is classified as Eye Irritant Category 2, Skin Sensitizer Category 1, and Aquatic Chronic Category 2. The substance is not listed as an SVHC (Substance of Very High Concern). Users must follow safety data sheet requirements and workplace exposure guidelines.

Where to buy [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate in Europe?

[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate is available through OYSI, a specialized European distributor of chemical products. OYSI provides this compound to pharmaceutical companies, research institutions, and chemical manufacturers across Europe. Contact OYSI directly for availability, specifications, and technical support. Ensure proper documentation and compliance with local regulations when ordering this classified chemical substance for your specific applications.

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[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate is a dangerous good. We support you with labeling, packaging, and transport documentation.

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Data Sources

Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.