(±)-Z-α-Phosphonoglycine trimethyl ester
(±)-Z-α-Phosphonoglycine trimethyl ester (CAS: 88568-95-0) is a chemical compound with a molecular weight of 331.26. This phosphonate ester serves as a key starting material in organic synthesis, particularly for the preparation of Z-dehydroamino acids through Wittig-Horner reactions with aldehydes. The resulting dehydroamino acids can then be stereoselectively reduced to yield valuable amino acid derivatives. Its utility lies in enabling precise chemical transformations in the fields of chemical biology and peptide chemistry.
- IUPAC
- (±)-Methyl 2-benzyloxycarbonylamino-2-(dimethoxyphosphinyl) acetate,(±)-Trimethyl Z-α-phosphonoglycinate
- Synonyms
- (±)-Methyl 2-benzyloxycarbonylamino-2-(dimethoxyphosphinyl) acetate(±)-Trimethyl Z-α-phosphonoglycinate
Synthesis of Z-Dehydroamino Acids
This compound is a crucial starting material for synthesizing (Z)-dehydroamino acids. It reacts with aldehydes via the Wittig-Horner reaction to form the desired unsaturated amino acid derivatives.
Preparation of Amino Acids
The (Z)-dehydroamino acids produced from the Wittig-Horner reaction can be stereoselectively reduced. This process allows for the controlled synthesis of specific amino acid stereoisomers.
Peptide Chemistry
As a glycine derivative and unnatural amino acid precursor, it finds application in advanced peptide chemistry for the incorporation of modified amino acid residues.
Chemical Biology Research
Its role as a building block for unnatural amino acids makes it a valuable reagent in chemical biology for studying protein function and developing novel biomolecules.
| Molecular weight | 331.26 |
|---|---|
| Linear formula | (CH3O)2P(O)CH(NHCO2CH2C6H5)CO2CH3 |
| Assay | ≥97.0% (HPLC) |
| Application | Starting material for the synthesis of (Z)-dehydroamino acids by Wittig-Horner reaction with aldehydes; the dehydroamino acids can be stereoselectively reduced to amino acids. |
| Melting point | 77-80 °C(lit.)78-80 °C |
Hazard statements
- H302Harmful if swallowed
| Protective equipment | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 22 |
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 (±)-Z-α-Phosphonoglycine trimethyl ester used for?
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(±)-Z-α-Phosphonoglycine trimethyl ester is used as a starting material for the synthesis of (Z)-dehydroamino acids via Wittig-Horner reactions with aldehydes. These dehydroamino acids can then be stereoselectively reduced to amino acids. It is valuable in peptide chemistry and chemical biology.
What is the CAS number and molecular formula?
+
The CAS number for (±)-Z-α-Phosphonoglycine trimethyl ester is 88568-95-0. The linear formula is (CH3O)2P(O)CH(NHCO2CH2C6H5)CO2CH3.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies (±)-Z-α-Phosphonoglycine trimethyl ester with an assay of ≥97.0% by HPLC. This product is supplied for research and development purposes and is not represented as USP, BP, EP, or pharmacopoeia grade.
What are the safety and handling recommendations?
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This compound is classified as harmful if swallowed (H302). When handling, it is recommended to use a dust mask type N95 (US), eyeshields, face shields, and gloves. Store in a cool, dry place.
How is this product packed and shipped?
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Products are carefully packed according to international shipping regulations and quality standards. As a global supplier and exporter, Tech Serve Solutions ensures compliant and secure dispatch.
How can I request a sample or quote?
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To request a sample or obtain a quote for (±)-Z-α-Phosphonoglycine trimethyl ester, please use the 'Request a Quote' or 'Sample Inquiry' form on our website or contact our sales team directly.
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