Synthesis of Vertex-Differentiated Icosahedral closo-Boranes: Polyfunctional Scaffolds for Targeted Drug Delivery

We report methods for the synthesis of vertex-differentiated icosahedral closo-boranes. A single B–OH vertex of the icosahedral borane [closo-B12(OH)12]2– was derivatized to prepare [closo-B12(OR)(OH)11]2– using optimized alkylation conditions and purification procedures. Several representative vert...

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Veröffentlicht in:	Journal of organic chemistry 2012-12, Vol.77 (24), p.11333-11338
Hauptverfasser:	Goswami, Lalit N, Houston, Zachary H, Sarma, Saurav J, Li, Hairong, Jalisatgi, Satish S, Hawthorne, M. Frederick
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkynes - chemistry Azides - chemistry B derivatives Boranes - chemical synthesis Boranes - chemistry Chemistry Chemistry Techniques, Synthetic Click Chemistry Drug Carriers - chemical synthesis Drug Carriers - chemistry Exact sciences and technology Organic chemistry Organometalloidal and organometallic compounds Preparations and properties
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Beschreibung
Zusammenfassung:	We report methods for the synthesis of vertex-differentiated icosahedral closo-boranes. A single B–OH vertex of the icosahedral borane [closo-B12(OH)12]2– was derivatized to prepare [closo-B12(OR)(OH)11]2– using optimized alkylation conditions and purification procedures. Several representative vertex-differentiated icosahedral closo-boranes were prepared utilizing carbonate ester and azide–alkyne click chemistries on the surface of the closo-B12 2– core.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo3021314