Transformations of chromanol and tocopherol and synthesis of ascorbate conjugates
摘要:
alpha-Tocopherol and as a model compound pentamethylchromanol could be transferred into simple and more complex 5a-ether derivatives including galactopyranose as well as ascorbic acid conjugates. Following elaboration of a glucopyranoside spacer element this could be used for tethering the vitamin E and the vitamin C components to give novel conjugates for subsequent biostudies concerning their proposed synergism of antioxidant properties in tissues. (C) 2011 Elsevier Ltd. All rights reserved.
PROBLEM TO BE SOLVED: To provide prodrugs of stereodefined oligonucleotides to impart additional stability to oligonucleotide molecules in many in-vitro and in-vivo applications.SOLUTION: A nucleic acid prodrug has a structure represented by the formula (1), where each instance of Ba is independently a blocked or unblocked adenine, cytosine, guanine, thymine, uracil or modified nucleobase.
α-Cyanoallyl acetate (1a), when treated with methanol in the presence of bis(acetonitrile)dichloropalladium(II) catalyst, is acetalized at the terminal olefinic carbon to give 1-cyano-3,3-dimethoxypropyl acetate (2). γ-Substituted α-cyanoallyl acetates give 3-substituted 1-cyano-3-oxo-propyl acetates 5 from which 2-cyanovinyl ketones 11 are obtained in good yields.
Described herein are nucleic acid prodrugs and nucleic acid prodrugs comprising chiral phosphorous moieties. Also described herein are methods of making and using nucleic acid prodrugs and nucleic acid prodrugs comprising chiral phosphorous moieties.