Anthraquinon-2-ylmethoxycarbonyl (Aqmoc): A New Photochemically Removable Protecting Group for Alcohols

Synthesis and photochemistry of a new photochemically removable protecting group for alcohols is described. Four carbonates of galactose derivatives (1−4) were synthesized from the corresponding arylmethanols via 4-nitrophenyl carbonate intermediates. Among them, photolysis of anthraquinon-2-ylmethoxycarbonyl (Aqmoc) galactose (1) proceeded with overall photolysis efficiency of 150 (quantum yield 0.10, and molar absorptivity 1500 M-1 cm-1) and rate constant of ∼106 s-1. To demonstrate its application to a biologically related molecule, 5‘-Aqmoc-adenosine (5) was synthesized and photolyzed to yield adenosine in 91% yield

Fluorescence Enhancement from Self-Assembled Aggregates: Substituent Effects on Self-Assembly of Azobenzenes

Fluorescence Enhancement from Self-Assembled Aggregates:  Substituent Effects on Self-Assembly of Azobenzene

Anthraquinon-2-ylmethoxycarbonyl (Aqmoc): A New Photochemically Removable Protecting Group for Alcohols

Synthesis and photochemistry of a new photochemically removable protecting group for alcohols is described. Four carbonates of galactose derivatives (1−4) were synthesized from the corresponding arylmethanols via 4-nitrophenyl carbonate intermediates. Among them, photolysis of anthraquinon-2-ylmethoxycarbonyl (Aqmoc) galactose (1) proceeded with overall photolysis efficiency of 150 (quantum yield 0.10, and molar absorptivity 1500 M-1 cm-1) and rate constant of ∼106 s-1. To demonstrate its application to a biologically related molecule, 5‘-Aqmoc-adenosine (5) was synthesized and photolyzed to yield adenosine in 91% yield

Synthesis and Characterization of Polyester Dendrimers from Acetoacetate and Acrylate

New aliphatic polyester-type dendrimers were synthesized using a new AB2-type building block 3, prepared from benzyl acetoacetate and 2 equiv of tert-butyl acrylate by acetoacetic acid ester synthesis. The reiterative [deprotection by HCO2H, then EDCI/DMAP coupling] sequence using divergent growth method gave [G1]-4tBu−[G5]-64tBu dendrimers. 13C NMR relaxation time (T1) measurements on the carboxy carbons show that the extended chain conformations are predominant in CDCl3