Boc-L-Tyr-ol: Properties, Uses & Handling FAQ

Boc-L-Tyr-ol is an N-Boc-protected L-tyrosinol derivative that serves as a versatile chiral amino alcohol building block in organic synthesis and pharmaceutical research.

Catalog SKU

B590275

Chemical class

N-Boc-protected amino alcohol derived from L-tyrosine

Stereochemistry

L-configuration (S) at the chiral center

Key functional groups

Boc carbamate (N-protection), primary alcohol, phenolic hydroxyl

Primary applications

Chiral building block in peptide and natural product synthesis; precursor for pharmaceutical intermediates

Recommended storage

Cool, dry conditions away from light; consult SDS for specific temperature requirements

What Is Boc-L-Tyr-ol and What Is Its Chemical Structure?

Boc-L-Tyr-ol, also referred to as N-Boc-L-tyrosinol, is the N-tert-butoxycarbonyl (Boc) protected form of L-tyrosinol (L-2-amino-3-(4-hydroxyphenyl)-1-propanol). It is a chiral amino alcohol that retains the (S)-stereocenter of the parent L-tyrosine amino acid. The molecule features three functional handles: a Boc-protected amine, a primary alcohol at C-1, and a free phenolic hydroxyl on the para-position of the benzene ring. This combination of protected amine and free hydroxyl groups makes it a highly selective and controllable synthetic intermediate for multi-step reactions.

What Are the Main Applications of Boc-L-Tyr-ol in Research?

Boc-L-Tyr-ol is primarily used as a chiral building block in the synthesis of complex molecules including peptidomimetics, natural product analogs, and pharmaceutical intermediates. The Boc group provides selective amine protection under mild conditions, allowing chemists to manipulate the alcohol or phenol moieties independently. Common uses include: (1) synthesis of chiral oxazolidinones and morpholine scaffolds via cyclization of the amino alcohol; (2) preparation of N-Boc-protected aminodiol intermediates; (3) construction of ligands for asymmetric catalysis; and (4) as a precursor in the total synthesis of tyrosine-derived natural products. Researchers in medicinal chemistry value this compound for its defined stereochemistry, which enables the preparation of enantiopure target molecules.

How Should Boc-L-Tyr-ol Be Stored and Handled Safely?

Boc-L-Tyr-ol should be stored under cool, dry conditions, protected from moisture and direct light, in a tightly sealed container. Users are strongly advised to consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for specific storage temperature, hazard classification, and personal protective equipment (PPE) requirements before handling. Standard laboratory precautions for organic reagents apply: use in a well-ventilated area or fume hood, wear appropriate gloves, eye protection, and lab coat. Avoid contact with strong oxidizing agents. If the compound is received as a solid, minimize exposure to atmospheric moisture to prevent degradation. Shelf life and specific handling conditions are detailed on the product SDS.

How Do I Order Boc-L-Tyr-ol from Aladdin Scientific?

Boc-L-Tyr-ol is available from Aladdin Scientific under catalog number B590275. To place an order, search for the SKU or product name on the Aladdin Scientific website, select the desired pack size and quantity, and proceed through the standard checkout process. Institutional purchase orders are accepted. For bulk quantities, custom pack sizes, or pricing inquiries, contact the Aladdin Scientific sales team directly. Registered account holders may also track orders, retrieve invoices, and access SDS documents through the online customer portal.

Quality, Purity and Specification Considerations

When selecting Boc-L-Tyr-ol for sensitive synthetic applications, researchers should verify purity grade and analytical certificates. Aladdin Scientific provides specification data including purity (typically assessed by HPLC or NMR), optical rotation to confirm enantiomeric integrity, and appearance. Researchers requiring high enantiopurity for asymmetric synthesis should request the Certificate of Analysis (CoA) for the specific lot number. Key quality parameters to review include: chemical purity (%), enantiomeric excess (ee%), optical rotation ([α]D), and water content if hygroscopic behavior is a concern. Contact Aladdin Scientific technical support for lot-specific documentation.

Frequently asked questions

What is the difference between Boc-L-Tyr-ol and L-tyrosinol?

L-tyrosinol is the unprotected amino alcohol derived by reduction of L-tyrosine, bearing a free primary amine, a primary alcohol, and a phenolic hydroxyl. Boc-L-Tyr-ol is the N-Boc-protected form in which the amine is masked as a tert-butoxycarbonyl carbamate, making it more stable and enabling chemoselective reactions at the alcohol or phenol without competing amine reactivity. The Boc group is easily removed under mild acidic conditions (e.g., TFA or HCl in dioxane) to regenerate the free amine when needed.

Can the Boc group be selectively removed without affecting the phenol or alcohol of Boc-L-Tyr-ol?

Yes. The Boc carbamate is selectively cleaved under acidic conditions, most commonly using trifluoroacetic acid (TFA) in dichloromethane or 4 M HCl in dioxane, which leave the primary alcohol and the phenolic hydroxyl intact. This orthogonality is one of the key synthetic advantages of the Boc protecting group strategy. Researchers should optimize deprotection conditions and reaction times for their specific substrate and downstream steps.

Is Boc-L-Tyr-ol suitable for use as a chiral auxiliary or ligand precursor?

Boc-L-Tyr-ol can serve as a precursor for chiral ligands and auxiliaries given its defined (S)-stereocenter and the presence of both nitrogen and oxygen donor atoms after deprotection. It has been used as a starting material for the synthesis of chiral oxazolidinones, amino diol ligands for metal-catalyzed asymmetric reactions, and other enantiopure scaffolds. Suitability for a specific application depends on the target structure; researchers are encouraged to review primary literature for precedents relevant to their synthetic goals.

What solvents are typically used to dissolve Boc-L-Tyr-ol?

Boc-L-Tyr-ol, as a polar amino alcohol derivative, is generally soluble in common organic solvents such as methanol, ethanol, dichloromethane, ethyl acetate, dimethylformamide (DMF), and dimethyl sulfoxide (DMSO). Solubility in non-polar solvents such as hexane is expected to be limited. Users should perform small-scale solubility tests under their specific experimental conditions. Avoid prolonged storage in protic solvents if stability is a concern.

How do I request a Certificate of Analysis (CoA) or Safety Data Sheet (SDS) for B590275?

Certificates of Analysis and Safety Data Sheets for Boc-L-Tyr-ol (B590275) can be downloaded directly from the Aladdin Scientific product page by entering the catalog number or lot number. If documents are not immediately available online, registered users may request them through the customer service portal or by contacting Aladdin Scientific support directly via email or phone.

References

1. General reference: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley-Interscience: New York, 2007. (Standard reference for Boc protecting group chemistry.)
2. Aladdin Scientific product page for Boc-L-Tyr-ol, SKU B590275. Aladdin Scientific Corp.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.