Name: Boc-D-Serine
CAS No.: 6368-20-3
EINECS No.: 444-670-6 (EC No.: 613-313-8)
Chemical Formula: C₈H₁₅NO₅
Molecular Weight: 205.21
InChI InChI=1S/C8H15NO5/c1-8(2,3)14-7(13)9-5(4-10)6(11)12/h5,10H,4H2,1-3H3,(H,9,13)(H,11,12)/t5-/m1/s1
Density 1.2977 g/cm³ (rough estimate); 1.2±0.1 g/cm³ (predicted value)
Boiling point 343.88°C (rough estimate); 385.1±37.0 °C at 760 mmHg
Flash point 186.7±26.5 °C
Water solubility: almost transparent; slightly soluble in DMSO and methanol
Vapor pressure 0.0±2.0 mmHg at 25°C
Refractive index 1.4540 (estimate); 1.486
Storage conditions Store in a cool, dry place away from light and sealed tightly.
Sensitivity: Sensitive to moisture (hygroscopic), stable under normal conditions.
Appearance: White solid or white to off-white powder.
Specific Gravity: 1.2977 (20°C).
Color: White.
BRN 1874714
MDL No. MFCD00063142
Hazard Symbols: Xi (irritant); GHS08 (health hazard).
Risk Terms: H318 (cause serious eye damage).
Safety Terms: S24/25 (avoid skin and eye contact); P280 (wear protective gloves/eye protection); P310 (call a doctor immediately); P305+P351+P338 (rinse eyes if in contact with eyes).
Customs Code: 29241990
II. Properties: Boc-D-serine is the N-tert-butoxycarbonyl (Boc) protected form of D-serine, and is a white crystalline powder or fine powder solid at room temperature. Its melting point is 91–95°C (literature values), specific rotation [α]D = +8.5° (c=1, H₂O), and optical rotation measured in DMF is 13.09° (C=0.4243 g/100mL, 20°C, 589 nm). This compound is stable at room temperature and pressure, with a pKa of 3.62±0.10 (predicted value), and is weakly acidic. Regarding solubility, it is almost insoluble in water, slightly soluble in DMSO and methanol, and soluble in alkaline aqueous solutions. Its vapor pressure is extremely low (0.0±2.0 mmHg at 25°C), and its flash point is 186.7±26.5°C. It is not classified as a flammable solid (WGK Germany: 3, storage category 13 – non-flammable solids).
III. Applications
Boc-D-serine is a key chiral building block in solid-phase peptide synthesis (SPPS) and liquid-phase organic synthesis. Its main applications include:
Peptide Drug Synthesis:As the Boc protected form of D-serine, it is widely used for fragment conjugation in GLP-1 class peptide drugs (such as semaglutide and telposide), anticonvulsants, and peptide-mimicking drugs, preventing the amino group from being affected by electrophilic reagents during conjugation.
Pharmaceutical Intermediate:** It is an important precursor for the synthesis of antiepileptic drugs such as acetylaminomethoxypropionic acid amide (deacetyldesmethyl lacosamide).
Chiral Catalysts and Ligands:** Used to prepare bioactive molecules and natural product analogs with specific stereoconfigurations.
Research Reagent:** As a high-purity amino acid derivative, it is used in molecular biology, pharmacology, and protein engineering research.
IV. Preparation Method
Industrially, a two-step process of enzymatic resolution + chemical protection is mainly used to prepare high optical purity products:
Step 1: Enzymatic Resolution of D-Serine
Under alkaline conditions, DL-serine and chloroacetyl chloride are used as raw materials for acylation. The reaction solution is evaporated to dryness under reduced pressure and then extracted with ethyl acetate. After decolorization with activated carbon, the extract is selectively enzymatically resolved by adding acylase I, hydrolyzing the L-type acylate, retaining the D-type acylate, and then purified to obtain D-serine with a high ee value.
Step 2: Boc Protection
The obtained D-serine is reacted with di-tert-butyl dicarbonate ((Boc)₂O) under alkaline conditions (such as NaOH/dioxane/water system) to protect the free amino group with a tert-butyloxycarbonyl group. After the reaction is complete, the product Boc-D-serine is obtained by acidification, extraction, and recrystallization (commonly using ethyl acetate/petroleum ether or ethyl acetate/n-hexane systems), with an overall yield of 75–85% and an optical purity ee ≥ 99%.
V. Safety Information
GHS Classification: Serious Eye Injury/Eye Irritation Category 1
Main Hazards: Solid; poses a serious risk of eye damage; may cause respiratory irritation
First Aid Measures: Inhalation: Move to fresh air; Skin Contact: Wash with soap and plenty of water; Eye Contact: Immediately flush with plenty of water for at least 15 minutes and seek medical attention; Ingestion: Rinse mouth, do not induce vomiting, seek immediate medical attention
Fire Control Measures: This product is a non-flammable solid. In case of fire, use water mist, dry powder, carbon dioxide, or alcohol-resistant foam to extinguish the fire.
Spill Handling: Collect the spilled material into a sealed container and clean it up with an inert absorbent material (such as sand, vermiculite). Avoid dust generation.
Handling Protection: Wear protective gloves, goggles, and a dust mask; operate in a fume hood; avoid inhaling dust and contact with eyes.
Incompatible Materials: Strong oxidizers
Decomposition Products: Carbon monoxide, carbon dioxide, nitrogen oxides
VI. Our Company’s Production Advantages and Capacity
6.1 Core Advantages
Technology Platform: Possesses a synthetic biology technology platform (enzyme catalysis, fermentation engineering) and Chiral chemistry technology platform (asymmetric synthesis, chiral resolution) ensures product optical purity (ee value ≥ 99.0%) and batch stability.
Green process: Enzymatic resolution replaces traditional chemical resolution, reducing organic solvent use and chiral waste emissions, meeting green chemistry and EHS requirements.
Quality control: Equipped with HPLC (chiral/chiral), GC, NMR, LC-MS, polarimeter, Karl Fischer moisture analyzer, etc.; strictly implements ISO 9001 and GMP-like quality management systems, providing COA, HPLC chromatograms, MSDS, and stable isotope internal standards.
Customized services: Supports customized synthesis from milligram (mg) to ton (ton) scale, and can provide targeted development of Boc-D-serine and its derivatives (such as Boc-D-Ser(Me)-OH, Boc-D-Ser(Bzl)-OH).
Stable supply chain: Long-term agreements have been signed with strategic suppliers for key raw materials (DL-serine, (Boc)₂O), resulting in high self-sufficiency and competitive pricing.
Compliant export. Familiar with major global market regulations (USP/EP/BP/CP), providing REACH pre-registration, DMF document support, and TSCA compliance services.
6.2 Production Capacity and Supply
Annual Production Capacity: 50 tons/year (expandable to 100 tons/year based on market demand)
Regular Inventory: 500 kg (standard packaging in 1kg, 5kg, and 25kg is readily available)
Packaging Specifications: 1g / 5g / 25g / 100g / 1kg / 5kg / 25kg / 50kg; double-layered PE bag lining, outer aluminum foil bag or cardboard drum/iron drum
Delivery Time: Spot goods: 3–5 working days; Bulk orders: 2–3 weeks; Custom synthesis: 4–6 weeks
Storage and Transportation: Sealed transport at room temperature (15–25°C), protected from light, no cold chain required; UN number and non-hazardous goods guarantee provided (air/sea freight as non-restricted goods)
Technical Support: 24-hour response to customer inquiries, providing support for scale-up process transfer, impurity profile analysis, and declaration document preparation.
Post time: Jun-04-2026
