Boc-Gly-OtBu

Boc-Gly-OtBu is a fundamental building block in Boc-strategy solid-phase peptide synthesis (SPPS), serving as the protected glycine derivative of choice for incorporating glycine residues into synthetic peptides and peptide-based therapeutics. The dual protection strategy — Boc on the amine and tert-butyl ester on the carboxylate — enables orthogonal deprotection, allowing Boc-Gly-OtBu to participate in sequential coupling reactions without premature chain termination or side reactions. In drug discovery programs, Boc-Gly-OtBu is employed in the synthesis of combinatorial peptide libraries, bioactive peptide analogs, and peptide-drug conjugates, where the controlled introduction of glycine residues is critical for achieving desired biological activity and conformational flexibility. Additionally, Boc-Gly-OtBu serves as a key intermediate in the development of antibody-drug conjugate (ADC) linkers and other bioconjugation strategies, where its orthogonal protection profile enables selective cleavage and functionalization. The crystalline solid form and high purity (>98% HPLC) of Boc-Gly-OtBu make it easy to handle, accurately weigh, and integrate into standard peptide synthesis workflows.

Product Parameters

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Parameter	Specification
Product Name	Boc-Gly-OtBu
CAS Number	111652-20-1
Molecular Formula	C₁₁H₂₁NO₄
Molecular Weight	231.29 g/mol
Appearance	White to almost white powder to crystal
Melting Point	66–68 °C (lit.)
Boiling Point	306.0±25.0 °C (predicted)
Density	1.023 g/cm³
Water Solubility	1.05 g/L at 20 °C
Solubility	Very soluble in methanol
Storage Condition	2-8℃

 

Synthetic Route

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＋→

Suspend glycine tert-butyl ester hydrochloride (10.0 g, 59.7 mmol) in toluene (46.2 ml), heat to 60 °C, then add triethylamine (6.51 g, 64.3 mmol) and stir for 0.5 hours. Subsequently, slowly add a solution of diisopropyl carbonate (10.0 g, 45.9 mmol) in Chemicalbook toluene (11.6 ml) to the reaction mixture and continue the reaction for another 6 hours. Upon completion, quench with water (30 ml) and separate the organic layer. The organic layer was subjected to azeotropic distillation with n-hexane to remove the solvent, yielding N-Boc-glycine tert-butyl ester (10.6 g, 45.9 mmol; yield 100%). The structure of the product was confirmed by 1H-NMR analysis.

 

FAQ

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Q1: What is Boc-Gly-OtBu?

A: Boc-Gly-OtBu (N-(tert-Butoxycarbonyl)glycine tert-butyl ester, CAS 111652-20-1) is a doubly protected glycine derivative featuring both a Boc protecting group on the amino group and a tert-butyl ester protecting group on the carboxylate. It is widely used as a building block in Boc-strategy solid-phase peptide synthesis.

 

Q2: What is the primary application of Boc-Gly-OtBu?

A: Boc-Gly-OtBu is primarily used as a building block in Boc-strategy solid-phase peptide synthesis (SPPS). It is also employed in the synthesis of combinatorial peptide libraries, peptide-drug conjugates, and antibody-drug conjugate (ADC) linkers.

 

Storage Conditions

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Store Boc-Gly-OtBu in a tightly sealed container in a dry, well-ventilated area at 2–8 °C. Alternatively, it may be stored at room temperature in a cool, dark place (<15 °C). Protect from moisture and light. The compound is stable under recommended storage conditions.

 

Shelf life: Please refer to the Certificate of Analysis for batch-specific expiration dating. Under recommended storage conditions, Boc-Gly-OtBu typically maintains >98% purity for 2–3 years.

 

Handling precautions: Use in a fume hood. Wear chemical-resistant gloves, safety goggles, and a lab coat. Avoid generating dust or aerosols. Do not eat, drink, or smoke in work areas. After handling, wash hands thoroughly. Refer to the Safety Data Sheet (SDS) for complete safety information.

 

Contact Us

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Whether you are scaling up a peptide manufacturing campaign, developing a novel peptide therapeutic, or simply need a reliable source of Boc-Gly-OtBu for your research, Cosperpharm is here to help. Reach out today for a quote, technical consultation, or custom packaging request — our team is ready to support your success.