The Synthesis of 9-(2-Amino-2-deoxy-β-D-allopyranosyl)-6-dimethylaminopurine, an Analog of the Aminonucleoside Derived from Puromycin

Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds

“…[(neocuproine)Pd(μ-OAc)] 2 (OTf) 2 was prepared according to the literature procedure. 35 Flash chromatography was performed on a Reveleris X2 Flash Chromatography, using Grace Reveleris Silica flash cartridges (4 g, 12 g, 15 g, 24 g, 40 g, 80 g, and 120 g) and Scorpius Diol (OH) 48 g. 1 H-, 13 C-, APT-, HSQC-, and COSY-NMR were recorded on a Varian AMX400 spectrometer (400, 100 MHz, respectively) using DMSO-d 6 , D 2 O, or methanol-d 4 as solvent. Chemical shift values are reported in ppm with the solvent resonance as the internal standard (DMSO-d 6 : δ 2.50 for 1 H, δ 39.52 for 13 C, CD 3 OD: δ 3.31 for 1 H, δ 49.15 for 13 C; D 2 O: δ 4.80 for 1 H).…”

“…35 Flash chromatography was performed on a Reveleris X2 Flash Chromatography, using Grace Reveleris Silica flash cartridges (4 g, 12 g, 15 g, 24 g, 40 g, 80 g, and 120 g) and Scorpius Diol (OH) 48 g. 1 H-, 13 C-, APT-, HSQC-, and COSY-NMR were recorded on a Varian AMX400 spectrometer (400, 100 MHz, respectively) using DMSO-d 6 , D 2 O, or methanol-d 4 as solvent. Chemical shift values are reported in ppm with the solvent resonance as the internal standard (DMSO-d 6 : δ 2.50 for 1 H, δ 39.52 for 13 C, CD 3 OD: δ 3.31 for 1 H, δ 49.15 for 13 C; D 2 O: δ 4.80 for 1 H). Data are reported as follows: chemical shifts (δ), multiplicity (s = singlet, d = doublet, dd = double doublet, ddd = double double doublet, t = triplet, appt = apparent triplet, q = quartet, m = multiplet), coupling constants J (Hz), and integration.…”

“…Allosamine forms the core component of the Chitinase inhibitor allosamidin . Lividosamine is part of the aminoglycosides lividomycin-A and -B and is a precursor for the antibiotic thienamycin. , As a building block for novel antibiotics and inhibitors, , ready access is highly relevant all the more so because allosamine and lividosamine are not commercially available. A downside of the reported routes is that even for these apparently simple transformations, epimerization of the hydroxyl group at C3 and deoxygenation, the number of reaction steps, often involving purification, is already considerable.…”

Glycosylated polyacrylate nanoparticles by emulsion polymerization

“…3-O-Acryloyl-1,2: Caraballo, de Paz & Galbis, 2000) and 4-N-acetyl-5'-O-acryloyl-2',3'-O-isopropylidene cytidine (10) (Cooper, Goody, Jones, Tittensor, & Walker, 1971) were prepared following the cited literature procedures. 1-O-Acryloyl-2,3,5-tri-O-benzyl-β-D-ribofuranose (6) and 2-Nacryloyl-1,3,4,6-tetra-O-benzoyl-β-D-glucosamine (7) were prepared from 2,3,5-tri-Obenzyl-β-D-ribofuranose (Barker & Fletcher, 1961) and 1,3,4,6-tetra-O-benzoyl-β-Dglucosamine hydrochloride (McEvoy, Weiss, & Baker, 1960), respectively, following similar acrylation procedures described in the synthesis of 5-O-acryloyl-2,3-isopropylidene-1-methoxy-β-D-ribofuranose (5). 1 H NMR and 13 C NMR spectra were recorded on Bruker DPX 250 and Varian Inova 400 NMR spectrometers.…”

Development of Highly PotentD-Glucosamine-Based Chiral Fluorescent Labeling Reagents and a Microwave-Assisted β-Selective Glycosidation of a Methyl Glycoside Reagent

“…The hydroxyl groups of N-acetyl D-glucosamine were all methylated 13,14) to give 1,3,4,6-tetra-O-methyl N-acetyl D-glucosamine in 51% yield. Following deacetylation of the D-glucosamine derivative, 15) an anthracenimide functionality was y To whom correspondence should be addressed. Tel: +81-22-717-8803; Fax: +81-22-717-8806; E-mail: ohrui@biochem.tohoku.ac.jp Biosci.…”