Methyl (S)-(−)-3-Boc-2,2-dimethyl-4-oxazolidinecarboxylate
Methyl (S)-(−)-3-Boc-2,2-dimethyl-4-oxazolidinecarboxylate (CAS: 108149-60-6) is a chiral auxiliary and oxazolidinone derivative. With a molecular weight of 259.30 g/mol, this compound serves as a key precursor in asymmetric synthesis. It is instrumental in the preparation of valuable molecules, including serinal derivatives, azasugars, and sphingolipids, and has been utilised in the synthesis of complex natural products.
- IUPAC
- Methyl (S)-(−)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate
- Synonyms
- Methyl (S)-(−)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate
Precursor for Garner's Aldehyde Synthesis
This oxazolidinone derivative is a vital precursor to Garner's aldehyde, a configurationally stable serinal derivative. Garner's aldehyde is widely employed in the synthesis of amino acids and related chiral building blocks.
Synthesis of Azasugars and Sphingolipids
The compound facilitates the construction of complex molecules such as azasugars and sphingolipids. These classes of compounds have significant biological relevance and are targets in medicinal chemistry research.
Antitumor Agent Synthesis
It has been used in the synthesis of the amino sugar component of calicheamicin, a potent antitumor agent. This highlights its importance in developing advanced therapeutic compounds.
| Molecular weight | 259.30 |
|---|---|
| Empirical formula | C12H21NO5 |
| Assay | 98% |
| Boiling point | 101-102 °C/2 mmHg(lit.) |
| Density | 1.082 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.443(lit.) |
| Optical activity | [α]20/D −55°, c = 1.3 in chloroform |
| Optical purity | ee: 99% (HPLC) |
| Application | Precursor to a configurationally stable serinal derivative (Garner′s aldehyde) that has been used to make azasugars, sphingolipids, and the amino sugar found in calicheamicin, a potent antitumor agent.1,2,3,4,5 |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 93 °C / 199.4 °F |
| Transport (UN / ADR) | NA 1993 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Methyl (S)-(−)-3-Boc-2,2-dimethyl-4-oxazolidinecarboxylate used for?
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Methyl (S)-(−)-3-Boc-2,2-dimethyl-4-oxazolidinecarboxylate is primarily used as a precursor in asymmetric synthesis, particularly for creating Garner's aldehyde, azasugars, sphingolipids, and components of antitumor agents like calicheamicin.
What is the CAS number and formula for this chemical?
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The CAS number is 108149-60-6, and its empirical formula (Hill notation) is C12H21NO5.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this chemical with an assay of 98%. We do not represent this product as USP, EP, BP, or any other pharmacopoeia grade.
How should this chemical be handled safely?
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This compound is a Warning substance (GHS07) and is harmful if inhaled, causes skin irritation, and serious eye irritation (H315-H319-H335). Handle with appropriate personal protective equipment, including eyeshields, gloves, and a suitable respirator. Ensure adequate ventilation.
How is this product packed and shipped?
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This chemical is packed according to international shipping regulations for hazardous materials. It is exported globally by Tech Serve Solutions, a licensed exporter since 1998.
How can I request a quote or sample?
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To request a quote or a sample, please visit the Tech Serve Solutions website or contact our sales department directly with your specific requirements.
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