34904-91-1Relevant articles and documents
Improved polyaromatic benzoin photoremovable protecting groups
Branda, Neil R.,Carling, Carl-Johan,McKay, Laura J.
, (2021/09/16)
Two novel photoremovable protecting groups in the benzoin class have been prepared and their photochemistry investigated. These polyaromatic benzoin photoremovable protecting groups have significantly improved molar extinction coefficients with absorption
Modulated photochemical reactivities of: O -acetylated (3′,5′-dimethoxyphenyl)heteroaryl acyloin derivatives under direct irradiation and photo-induced electron transfer conditions
Bisht, Rajesh,Singh, Saumya,Krishnamoorthy, Kothandam,Nithyanandhan, Jayaraj
, p. 835 - 845 (2018/06/21)
3′,5′-Dimethoxybenzoin esters are important photoremovable protecting groups which form 2-phenylbenzofuran derivatives upon photo-release. We utilized a similar concept to test a photochemical method of installing a benzofuran moiety to the conjugated bac
Photoacylation of alcohols in neutral medium
Debieux, Jean-Luc,Cosandey, Anne,Helgen, Celine,Bochet, Christian G.
, p. 2073 - 2077 (2008/02/04)
We report here conditions which allow the photoacylation of primary, secondary and tertiary alcohols with N-acetyl-5,7-dinitroindoline under exceptionally mild conditions, at wavelengths harmless to most functional groups, including otherwise photosensitive ones. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Mechanistic studies on the photochemical deprotection of 3′,5′-dimethoxybenzoin esters
Pirrung, Michael C.,Ye, Tong,Zhou, Zheng,Simon, John D.
, p. 1258 - 1264 (2008/02/12)
Several mechanistic alternatives proposed for the photochemical deprotection of dimethoxybenzoin esters are presented. Both experimental and theoretical evidence suggest the mechanism is heterolysis of the singlet excited state to form a carboxylate and t
Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin
Pirrung, Michael C.,Shuey, Steven W.
, p. 3890 - 3897 (2007/10/02)
Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically.These compounds can be useful in light-directed synthesis and caging.The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields.Two groups, 2',3'-dimethoxybenzoin and 3',5'-dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters.These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism.An asymmetric synthesis of 3',5'-dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols.A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives.These compounds were deprotected photochemically to produce the phosphodiesters in high yield.