Boc-alpha-phosphonoglycine trimethyl ester

Boc-α-phosphonoglycine trimethyl ester (CAS 89524-98-1) is a strategically protected phosphonate amino acid derivative optimized for peptide mimetic synthesis and enzyme inhibitor development. This molecule features three orthogonal functional elements: a Boc (tert-butoxycarbonyl) protecting group enabling acid-labile amine deprotection under mild conditions, an α-phosphonate moiety that mimics phosphate transition states with superior metabolic stability compared to natural phosphates, and a trimethyl ester configuration that enhances lipophilicity for improved cellular uptake. The phosphonate group—resistant to phosphatase-mediated hydrolysis while maintaining key hydrogen-bonding geometry—positions this intermediate as a versatile scaffold for protease inhibitor design, prodrug strategies, and phosphonopeptide therapeutics targeting metalloenzymes or kinase pathways. Manufactured with purity ≥98% under controlled conditions, it supports medicinal chemistry programs where phosphate mimicry combined with orthogonal protection is essential for structure-activity relationship studies.

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Product Name	Boc-α-phosphonoglycine trimethyl ester
CAS Number	89524-98-1
Chinese Name	Boc-α-膦酰基甘氨酸三甲酯
Synonyms	tert-Butoxycarbonyl-α-phosphonoglycine trimethyl ester; Boc-α-phosphonoglycine methyl ester; (tert-Butoxycarbonylamino)(dimethoxyphosphoryl)acetic acid methyl ester; MFCD02685915
Chinese Synonyms	叔丁氧羰基-α-膦酰甘氨酸三甲酯; Boc-α-膦酰基甘氨酸甲酯; 叔丁氧羰基氨基膦酰乙酸甲酯; 膦酰氨基酸保护衍生物
Molecular Formula	C₁₀H₂₀NO₇P
Molecular Weight	297.24 g/mol
Purity	≥ 98% (HPLC area normalization)
Product Category	Pharmaceutical Intermediates / Phosphonate Amino Acids / Boc-Protected Building Blocks
Appearance	White to Off-white Crystalline Powder or Viscous Oil
Storage Conditions	Store in a cool, dry, well-ventilated area away from light and moisture. Keep container tightly closed under inert atmosphere (nitrogen). Protect from strong acids to avoid premature Boc deprotection.
Shelf Life	18-24 months under recommended storage conditions
Packaging	100mg/vial, 500mg/vial, 1g/bottle, 5g/bottle, or customized according to customer requirements
Applications	Phosphonopeptide synthesis, protease inhibitor development, prodrug design, transition-state analog research, metalloenzyme targeting, kinase pathway modulation, antiviral drug intermediates, bone metabolism modulator precursors
Reactivity	Suitable for selective Boc deprotection (TFA or HCl/dioxane), phosphonate ester hydrolysis to mono/di-acid forms, amide coupling at the carboxylate, phosphonate-directed metal coordination, and orthogonal deprotection strategies