title: Efficient synthesis of 2'-C-α-aminomethyl-2'-deoxynucleosides.
abstract: Starting from methyl 3,5-di-O-benzyl-2-keto-α-D-ribofuranoside, a convergent, six-step synthesis is developed to give efficiently all four 2'-C-α-aminomethyl-2'-deoxynucleosides (U, C, A, G) in 38%, 42%, 12%, 12% yield, respectively. Convergence is achieved by the glycosylation of persilylated nucleobases with methyl 2-α-phthalimidomethyl ribofuranoside.
authors: Department of Biochemistry & Molecular Biology, University of Chicago, 929 East 57th Street, Chicago, Illinois 60637, USA. nli@uchicago.edu
authors: Nan-Sheng
authors: NS
authors: Li
authors: Joseph A
authors: JA
authors: Piccirilli
mesh_terms: D006031:Glycosylation; D009705:Nucleosides / Q000138:chemical synthesis*; D011687:Purines / Q000737:chemistry*; D011741:Pyrimidine Nucleosides; D011743:Pyrimidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009705:Nucleosides; D011687:Purines; D011741:Pyrimidine Nucleosides; D011743:Pyrimidines