Name: C2-Bis-phosphoramidic acid diethyl ester
Brand: BOC Sciences
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IUPACName

N,N'-bis(diethoxyphosphoryl)ethane-1,2-diamine

InChI Key

NGADUQWRPABXQB-UHFFFAOYSA-N

InChI

InChI=1S/C10H26N2O6P2/c1-5-15-19(13,16-6-2)11-9-10-12-20(14,17-7-3)18-8-4/h5-10H2,1-4H3,(H,11,13)(H,12,14)

SMILES

CCOP(=O)(NCCNP(=O)(OCC)OCC)OCC

1. Dimethyl and diethyl esters of 5,6-bis-(pyridin-2-yl)pyrazine-2,3-di-carb-oxy-lic acid: a comparison

Montserrat Alfonso, Helen Stoeckli-Evans Acta Crystallogr E Crystallogr Commun. 2016 Jan 27;72(Pt 2):233-7.doi: 10.1107/S2056989016001080.eCollection 2016 Feb 1.

In dimethyl 5,6-bis-(pyridin-2-yl)pyrazine-2,3-di-carboxyl-ate, C18H14N4O4, (I), and diethyl 5,6-bis-(pyridin-2-yl)pyrazine-2,3-di-carboxyl-ate, C20H18N4O4, (II), the dimethyl and diethyl esters of 5,6-bis-(pyridin-2-yl)pyrazine-2,3-di-carb-oxy-lic acid, the orientation of the two pyridine rings differ. In (I), pyridine ring B is inclined to pyrazine ring A by 44.8 (2)° and the pyridine and pyrazine N atoms are trans to one another, while pyridine ring C is inclined to the pyrazine ring by 50.3 (2)°, with the pyridine and pyrazine N atoms cis to one another. In compound (II), the diethyl ester, which possesses twofold rotation symmetry, the pyridine ring is inclined to the pyrazine ring by 40.7 (1)°, with the pyridine and pyrazine N atoms trans to one another. In the crystal of (I), mol-ecules are linked by C-H⋯N hydrogen bonds, forming chains along [001]. The chains are linked by C-H⋯π inter-actions, forming a three-dimensional structure. In the crystal of (II), mol-ecules are linked via C-H⋯O hydrogen bonds, forming a three-dimensional framework. There are C-H⋯π inter-actions present within the framework.

C2-Bis-phosphoramidic acid diethyl ester, provides a versatile phosphorylated handle for assembling targeted protein degraders. Its phosphoramidate functionality supports modular conjugation strategies, enabling researchers to integrate ligand motifs while maintaining chemical stability during linker synthesis and subsequent PROTAC construction. The molecule’s reactivity profile is well suited to stepwise synthetic workflows, and the

Structure: The linker contains a bis-phosphoramidate framework bearing diethyl ester groups and nitrogen-bound phosphorus centers. It features P–N and P–O connectivity, with phosphoryl-derived electronic character that can influence solubility and hydrolytic behavior. The presence of ester substituents contributes to controlled stability prior to downstream functionalization.

Reactivity: Phosphoramidate ester linkers are commonly used under nucleophilic substitution or activation conditions to enable coupling to amine or alcohol-containing partners in PROTAC assembly. Typical approaches rely on base-mediated deprotection or electrophile activation, often using inert atmosphere, anhydrous polar organic solvents, and carefully controlled moisture levels to minimize premature hydrolysis. Catalysts are selected based on the target functional group compatibility, following established phosphoramidate chemistry principles.

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It is commonly abbreviated as: C₁V₁ = C₂V₂