Phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

Name: Phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate
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CAS No. 379270-35-6
Cat. No. CS-W004381
Purity≥97%
MDL No.MFCD28386144

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Phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate|CS-W004381

Structure of 379270-35-6

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Description

This phenyl hydrogen phosphonate derivative integrates a purine nucleobase with a chiral propanol linker, enabling site-specific conjugation in nucleoside analog synthesis. The pendant amino group supports further functionalization, while the phosphonate moiety enhances metabolic stability and cell permeability for applications in antiviral and anticancer research.

Application

Phenyl hydrogen (((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate serves as a key building block for nucleoside analog synthesis, enabling efficient phosphorylation at the 5′-position. Its chiral propanediol linker provides stereocontrol in glycosylation reactions, while the purine amine group allows direct functionalization for antiviral and anticancer scaffold development. The phosphonate moiety offers enhanced metabolic stability and facilitates coupling under standard Mitsunobu or amide bond-forming conditions.

General Information

CAS No. 379270-35-6
Cat. No. CS-W004381
Purity ≥97%
MDL No. MFCD28386144
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₈N₅O₄P
Molecular Weight 363.31
Synonym(s) None
SMILES C[C@@H](OCP(OC1=CC=CC=C1)(O)=O)CN2C=NC3=C(N)N=CN=C23

Computational Chemistry Data

TPSA 125.38
LogP 2.0355
H_Acceptors 8
H_Donors 2
Rotatable_Bonds 7

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Other Classifications

Building Blocks Functional Group Phosphate

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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Phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

CAS No. 379270-35-6

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