[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate
C13H25NO4Si
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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 chiral β-lactam intermediate featuring silyl protection groups and stereospecific configuration. This specialized organosilicon compound represents a sophisticated synthetic intermediate commonly utilized in pharmaceutical manufacturing and advanced organic synthesis. With its molecular formula C13H25NO4Si and molecular weight of 287.43 g/mol, this β-lactam derivative incorporates both a tert-butyldimethylsilyl (TBDMS) protecting group and an acetate functionality, making it particularly valuable for stereoselective transformations in complex molecule synthesis. The compound's three-dimensional structure, defined by its (2R,3R) and (1R) stereochemical descriptors, ensures precise spatial arrangement crucial for pharmaceutical applications where chirality determines biological activity. The presence of the four-membered azetidine ring system, characteristic of β-lactam chemistry, provides reactive sites for further synthetic elaboration while maintaining structural stability under appropriate conditions. From a safety perspective, this substance is classified under GHS as Eye Irritant Category 2, Skin Sensitizer Category 1, and Aquatic Chronic Category 2, requiring appropriate handling protocols including personal protective equipment and environmental precautions. The ADR Class 9 designation indicates miscellaneous dangerous goods classification for transportation purposes. Industrial applications primarily focus on pharmaceutical intermediate synthesis, particularly in the development of β-lactam antibiotics and related therapeutic compounds. The compound also finds utility in specialized organic synthesis where protected alcohol functionalities and controlled stereochemistry are essential. Unlike simpler compounds such as 2-methylpropyl 2-(oxiran-2-yl)acetate, this advanced intermediate offers sophisticated protection strategies for complex synthetic pathways. OYSI maintains reliable supply chains for this specialized pharmaceutical intermediate, supporting European chemical manufacturing with consistent quality and regulatory compliance.
Safety & Classification
Eye Irrit. 2; Skin Sens. 1; Aquatic Chronic 2
GHS Pictograms
HHazard Statements (H-Statements)
Describe the nature and severity of the hazard
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
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
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 Number | 3077 |
| ADR Class | 9 |
| Packing Group | III |
| Tunnel Code | - |
| Proper Shipping Name | (2R,3R)-3-((R)-1-(tert-Butyldimethylsiloxy)ethyl)-4-oxoazetidin-2-ylacetat |
| Marine Pollutant | No |
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 chiral molecule features a β-lactam (azetidinone) core structure protected with tert-butyldimethylsilyl and acetate groups. With a molecular weight of 287.43 g/mol, it is classified as a hazardous substance causing eye irritation and skin sensitization.
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 organic silyl ester compound with molecular formula C13H25NO4Si and molecular weight 287.43 g/mol. The presence of silyl protecting groups and acetate functionality suggests moderate lipophilicity and potential sensitivity to hydrolysis. Specific physical properties such as melting point, boiling point, and exact solubility data require laboratory determination or supplier specification sheets for precise values.
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. The β-lactam core structure and protective groups make it valuable for developing β-lactam antibiotics and related pharmaceutical compounds. Its specific stereochemistry (2R,3R,1R configuration) is crucial for synthesizing enantiomerically pure pharmaceutical products. It serves as a building block in medicinal chemistry and fine chemical manufacturing.
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. Wear appropriate personal protective equipment including safety goggles, chemical-resistant gloves, and protective clothing. Ensure adequate ventilation in work areas and avoid direct contact with skin and eyes. Handle in a well-ventilated area or under a fume hood to minimize inhalation exposure. Follow standard laboratory safety protocols when working with this compound.
How to store [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate properly?
[(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate should be stored in a cool, dry place away from heat sources and direct sunlight. Keep containers tightly sealed to prevent moisture ingress, which could cause hydrolysis of the silyl and acetate protecting groups. Store separately from strong acids, bases, and oxidizing agents. Maintain storage temperature as recommended by the supplier, typically under refrigerated conditions to ensure compound stability and prevent degradation.
What to do in case of contact with [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate?
Immediate first aid is essential following contact with [(2R,3R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate. For eye contact, rinse immediately with plenty of clean water for at least 15 minutes and seek medical attention. For skin contact, wash thoroughly with soap and water, and remove contaminated clothing. If inhaled, move to fresh air immediately. Due to its skin sensitization properties, monitor for allergic reactions and consult a physician if symptoms persist or worsen.
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 hazardous substance, it cannot be disposed of with regular laboratory waste. Contact authorized hazardous waste disposal companies for proper collection and treatment. Ensure proper labeling of waste containers with compound identification and hazard information. Small quantities may be suitable for controlled incineration at high temperatures in specialized 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 substances), Packing Group III for transportation. This classification requires appropriate packaging, labeling, and documentation according to ADR regulations for road transport in Europe. Use UN-approved packaging and ensure proper hazard labels are affixed. Transport documentation must include the compound's identification, hazard class, and emergency response information. Follow all applicable dangerous goods transportation regulations.
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 not classified as a Substance of Very High Concern (SVHC) under REACH regulation. However, it is subject to CLP regulation classification as Eye Irritant Category 2, Skin Sensitizer Category 1, and Aquatic Chronic Category 2. Suppliers must provide Safety Data Sheets and appropriate hazard labeling with GHS07 and GHS09 pictograms. Users must comply with occupational safety regulations and environmental protection requirements in their respective jurisdictions.
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 leading European distributor of specialty chemicals and pharmaceutical intermediates. OYSI provides this compound with complete documentation including Safety Data Sheets, Certificates of Analysis, and regulatory compliance information. As a specialized chemical intermediate, availability may be subject to minimum order quantities and lead times. Contact OYSI directly for current pricing, specifications, and delivery options to your location within Europe.
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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.
Data Sources
Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.