Overview and Chemical Properties

(R)-2-N-Cbz-amino-pentane-1,5-diol (Aladdin SKU B700269) is a bifunctional chiral compound bearing two hydroxyl groups at positions 1 and 5, and a benzyloxycarbonyl (Cbz)-protected amine at position 2. The (R)-stereocenter at C-2 confers defined chirality, making this compound a valuable precursor for stereoselective synthesis.

The Cbz group is one of the most widely used amine-protecting groups in synthetic chemistry. It is stable under basic conditions and can be cleanly removed by catalytic hydrogenolysis (e.g., Pd/C, H₂) or by strong acids (e.g., HBr/AcOH), providing orthogonal deprotection strategies when combined with other protecting groups.

The presence of two free hydroxyl groups allows selective functionalization: the less hindered primary alcohol at C-5 can often be distinguished from the C-1 hydroxyl through steric or electronic differentiation, enabling regioselective transformations such as tosylation, mesylation, or oxidation.

Note: Molecular weight, exact CAS number, and purity specifications should be verified against the current Aladdin Scientific Certificate of Analysis (CoA) for lot B700269.

Storage and Safety Precautions

Storage: Store (R)-2-N-Cbz-amino-pentane-1,5-diol under cool (2–8 °C), dry, and dark conditions. For long-term storage, an inert atmosphere (argon or nitrogen) is recommended to minimize oxidative degradation. Always reseal the container tightly after each use.

Handling: Work in a well-ventilated fume hood. Wear appropriate personal protective equipment (PPE) including chemical-resistant gloves, lab coat, and safety glasses. Avoid contact with skin, eyes, and mucous membranes.

Disposal: Dispose of waste material in accordance with local, regional, and national regulations governing organic chemical waste. Do not pour down the drain.

Important: Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific for SKU B700269 before use. Specific hazard classifications, first-aid measures, and regulatory information are detailed therein.

Recommended Synthetic Applications

(R)-2-N-Cbz-amino-pentane-1,5-diol is routinely employed as a chiral building block in multi-step synthesis. Key applications include:

• Synthesis of chiral pyrrolidines and piperidines: Selective activation of one hydroxyl group (e.g., as a mesylate or tosylate) followed by intramolecular N-alkylation after Cbz removal can yield enantiomerically pure cyclic amines, which are key scaffolds in medicinal chemistry.
• Natural product synthesis: The 1,2-amino alcohol and 1,5-diol motifs present in this compound are found in a wide range of biologically active natural products. This building block can serve as the starting material for fragment coupling strategies.
• Orthogonal protection strategies: The Cbz-protected nitrogen and free hydroxyl groups can be independently manipulated using well-established protecting group chemistry, enabling complex molecule construction.
• Asymmetric synthesis: The defined (R)-stereocenter can be used to transfer chirality to newly formed stereocenters in subsequent steps via substrate-controlled reactions.

Note: Specific reaction conditions, yields, and literature precedents for each application should be verified in the primary literature before use in a research setting.

Step-by-Step Handling Protocol

Follow these steps to ensure safe, effective use of (R)-2-N-Cbz-amino-pentane-1,5-diol (SKU B700269):

1. Pre-use preparation: Remove the vial from cold storage and allow it to equilibrate to room temperature before opening to prevent condensation of atmospheric moisture onto the compound.
2. Opening and weighing: Open the vial in a dry, inert-atmosphere glovebox or under a gentle stream of dry nitrogen if the compound is moisture-sensitive (confirm in SDS). Tare an appropriate vessel and weigh the desired quantity using an analytical balance.
3. Dissolution: Dissolve the compound in a suitable anhydrous solvent. Common choices for amino diol derivatives include dichloromethane (DCM), tetrahydrofuran (THF), dimethylformamide (DMF), or methanol, depending on the downstream reaction requirements. Verify solubility data in the CoA or primary literature.
4. Reaction setup: Use standard Schlenk or inert-atmosphere techniques if the subsequent chemistry requires exclusion of air or moisture. Confirm compatibility of the compound with all reagents before combining.
5. Cbz deprotection (if required): Remove the Cbz group by catalytic hydrogenolysis using Pd/C (typically 10 wt%) under H₂ (1 atm) in a protic solvent such as ethanol or methanol. Alternatively, treat with HBr in acetic acid. Filter catalyst through Celite before workup.
6. Workup and purification: After the reaction, perform standard aqueous workup appropriate to the reaction conditions. Purify the product by column chromatography (silica gel), recrystallization, or other appropriate techniques. Monitor by TLC or HPLC.
7. Resealing and storage: Return any unused compound to its original container, seal under inert gas, and store at 2–8 °C as specified.

Quality Control and Analytical Characterization

To confirm identity and purity of (R)-2-N-Cbz-amino-pentane-1,5-diol upon receipt and after storage, the following analytical methods are recommended:

• TLC: Run on silica gel plates using an appropriate eluent system (e.g., EtOAc/hexane mixtures). Visualize with UV (254 nm) and/or KMnO₄ staining.
• ¹H NMR and ¹³C NMR: Confirm structural identity and assess purity. Key signals include the Cbz carbamate NH, OCH₂ of the benzyl group (~5.1 ppm), and the methine proton at C-2.
• Optical rotation: Measure [α]D to verify the (R)-configuration and compare with the value reported on the CoA. A significant deviation may indicate racemization or degradation.
• HPLC: Use a chiral stationary phase (CSP) column or an achiral reversed-phase column with UV detection to assess chemical purity and, where applicable, enantiomeric excess (ee).
• Mass spectrometry (MS): Confirm the molecular ion and fragmentation pattern consistent with the expected molecular formula.

Note: Specific acceptance criteria, reference optical rotation values, and NMR chemical shift assignments should be taken from the Aladdin Scientific CoA for lot B700269. All analytical parameters listed here are standard practice for amino diol derivatives and should be adapted to the specific instrument and method validated in your laboratory.