172291-77-9Relevant academic research and scientific papers
Catalyst recognition of cis-1,2-diols enables site-selective functionalization of complex molecules
Sun, Xixi,Lee, Hyelee,Lee, Sunggi,Tan, Kian L.
, p. 790 - 795 (2013/09/23)
Carbohydrates and natural products serve essential roles in nature, and also provide core scaffolds for pharmaceutical agents and vaccines. However, the inherent complexity of these molecules imposes significant synthetic hurdles for their selective functionalization and derivatization. Nature has, in part, addressed these issues by employing enzymes that are able to orient and activate substrates within a chiral pocket, which increases dramatically both the rate and selectivity of organic transformations. In this article we show that similar proximity effects can be utilized in the context of synthetic catalysts to achieve general and predictable site-selective functionalization of complex molecules. Unlike enzymes, our catalysts apply a single reversible covalent bond to recognize and bind to specific functional group displays within substrates. By combining this unique binding selectivity and asymmetric catalysis, we are able to modify the less reactive axial positions within monosaccharides and natural products.
Regioselective monoacetylation of methyl pyranosides of pentoses and 6-deoxyhexoses by acetic anhydride in the presence of MoCl5
Evtushenko, Evgeny V.
, p. 1593 - 1599 (2007/10/03)
Convenient regioselective syntheses of 3-acetates of methyl pyranosides of α-L-rhamnose, α- and β-L-arabinose, α-D-fucose, α-D-lyxose, and β-D-ribose with good yields have been attained using MoCl5 as catalyst. Methyl β-L-rhamnopyranoside under this conditions gave 2-acetate. Copyright Taylor & Francis Group, LLC.
