{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T20:14:32Z","timestamp":1760645672738},"reference-count":30,"publisher":"CLOCKSS Archive","issue":"1","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["HETEROCYCLES"],"published-print":{"date-parts":[[2005]]},"DOI":"10.3987\/com-05-s(k)36","type":"journal-article","created":{"date-parts":[[2009,3,23]],"date-time":"2009-03-23T00:53:45Z","timestamp":1237769625000},"page":"361","source":"Crossref","is-referenced-by-count":29,"title":["Synthesis of Base-selectively Deuterium-labelled Nucleosides by the Pd\/C-catalyzed H-D Exchange Reaction in Deuterium Oxide"],"prefix":"10.13030","volume":"66","author":[{"given":"Hironao","family":"Sajiki","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroyoshi","family":"Esaki","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fumiyo","family":"Aoki","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tomohiro","family":"Maegawa","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kosaku","family":"Hirota","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"5187","reference":[{"key":"#cr-split#-10.3987\/COM-05-S(K)36-1.1","doi-asserted-by":"crossref","unstructured":"(a) \u2018Chemistry of Nucleosides and Nucleotides,\u2019 ed. by L. B. Townsend, Plenum Press, New York, 1988;","DOI":"10.1007\/978-1-4613-0995-6"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-1.2","doi-asserted-by":"crossref","unstructured":"(b) C. Perigaud, G. Gosselin, and J. L. Imbach, Nucleosides and Nucleotides, 1992, 11, 903;","DOI":"10.1080\/07328319208021748"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-1.3","doi-asserted-by":"crossref","unstructured":"(c) \u2018Nucleosides and Nucleotides as Antitumor and Antiviral Agents,\u2019 ed. by C. K. Chu and D. C. Baker, Plenum Press, New York, 1993;","DOI":"10.1007\/978-1-4615-2824-1"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-1.4","doi-asserted-by":"crossref","unstructured":"(d) K. Haraguchi, Y, Itoh, and H. Tanaka, J. Synth. Org. Chem., Jpn., 2003, 61, 974;","DOI":"10.5059\/yukigoseikyokaishi.61.974"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-1.5","doi-asserted-by":"crossref","unstructured":"(e) A. Matsuda and T. Sasaki, Cancer Sci., 2004, 95, 105.","DOI":"10.1111\/j.1349-7006.2004.tb03189.x"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-2.1","doi-asserted-by":"crossref","unstructured":"(a) T. Junk and W. J. Catallo, Chem. Soc. Rev., 1997, 26, 401;","DOI":"10.1039\/CS9972600401"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-2.2","doi-asserted-by":"crossref","unstructured":"(b) N. Elander, J. R. Jones, S. -Y. Lu, and S. Stone-Elander, Chem. Soc. Rev., 2000, 29, 239;","DOI":"10.1039\/a901713e"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-2.3","doi-asserted-by":"crossref","unstructured":"(c) A. Durazo and M. M. Abu-Omar, Chem. Commun., 2002, 66;","DOI":"10.1039\/b108864e"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-2.4","doi-asserted-by":"crossref","unstructured":"(d) D. Gani and D. W. Young, J. Chem, Soc., Chem. Commun., 1983, 576;","DOI":"10.1039\/C39830000576"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-2.5","doi-asserted-by":"crossref","unstructured":"(e) D. Gani, P. B. Hitchcock, and D. W. Young, J. Chem, Soc., Chem. Commun., 1983, 898.","DOI":"10.1039\/c39830000898"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-3.1","doi-asserted-by":"crossref","unstructured":"(a) E. Kawashima, Y. Aoyama, T. Sekine, M. Miyahara, M. F. Radwan, E. Nakamura, M. Kainosho, Y. Kyogoku, and Y. Ishido, J. Org. Chem., 1995, 60, 6980;","DOI":"10.1021\/jo00126a058"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-3.2","doi-asserted-by":"crossref","unstructured":"(b) A. F\u00f6ldesi, A. Trifonova, Z. Dinya, and J. Chattopadhyaya, J. Org. Chem., 2001, 66, 6560.","DOI":"10.1021\/jo010097n"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-4.1","doi-asserted-by":"crossref","unstructured":"(a) R. K. Hill, N. D. Ledford, and L. A. Renbaum, J. Labelled. Compds. Radiopharm, 1985, 22, 143;","DOI":"10.1002\/jlcr.2580220207"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-4.2","doi-asserted-by":"crossref","unstructured":"(b) T. Fujii, T. Saito, K. Kizu, H. Hayashibara, Y. Kumazawa, S. Nakajima, and T. Fujisawa, Chem. Pharm. Bull., 1991, 39, 301; (b) M. Sako, T. Hayashi, K. Hirota, and Y. Maki, Chem. Pharm. Bull., 1992, 40, 1656.","DOI":"10.1248\/cpb.39.301"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-5.1","doi-asserted-by":"crossref","unstructured":"(a) G. Guroff, C. A. Reifsnyder, and J. Daly, Biochem. Biophys. Res. Commun., 1996, 24, 720;","DOI":"10.1016\/0006-291X(66)90384-6"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-5.2","doi-asserted-by":"crossref","unstructured":"(b) D. V. Santi and C. F. Brewer, J. Am. Chem. Soc., 1968, 90, 6236;","DOI":"10.1021\/ja01024a063"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-5.3","doi-asserted-by":"crossref","unstructured":"(c) M. Maeda, M. Saneyoshi, and Y. Kawazoe, Chem. Pharm. Bull., 1971, 19, 1641;","DOI":"10.1248\/cpb.19.1641"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-5.4","doi-asserted-by":"crossref","unstructured":"(d) M. Maeda and Y. Kawazoe, Tetrahedron Lett., 1975, 19, 1643;","DOI":"10.1016\/S0040-4039(00)72221-0"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-5.5","doi-asserted-by":"crossref","unstructured":"(e) J. L. Wong and J. H. Keck, Jr., J. Chem, Soc., Chem. Commun., 1975, 125;","DOI":"10.1039\/c39750000125"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-5.6","doi-asserted-by":"crossref","unstructured":"(f) R. Kiritani, T. Asano, S. Fujita, T. Dohmaru, and T. Kawanishi, J. Labelled. Compds. Radiopharm, 1986, 23, 207;","DOI":"10.1002\/jlcr.2580230211"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-5.7","unstructured":"(g) J. Rocek, V. Sv\u00c1ta, and L. Leseticky, Coll. Czech, Chem. Commun., 1985, 50, 1244."},{"key":"10.3987\/COM-05-S(K)36-6","unstructured":"6. D2 gas [$96.40\/10 L of D2 gas (Aldrich 36,186-0) in lecture bottle] is also purchased as a lecture bottle or cylinder charged by high-pressure."},{"key":"10.3987\/COM-05-S(K)36-7","doi-asserted-by":"crossref","unstructured":"7. H. Sajiki, K. Hattori, F. Aoki, K. Yasunaga, and K. Hirota, Synlett, 2002, 1149.","DOI":"10.1055\/s-2002-32605"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-8.1","doi-asserted-by":"crossref","unstructured":"(a) H. Sajiki, F. Aoki, H. Esaki, T. Maegawa, and K. Hirota, Org. Lett., 2004, 6, 1485;","DOI":"10.1021\/ol0496374"},{"key":"#cr-split#-10.3987\/COM-05-S(K)36-8.2","unstructured":"(b) T. Maegawa, A. Akashi, H. Esaki, F. Aoki, H. Sajiki, and K. Hirota, Synlett, 2005, 845."},{"key":"10.3987\/COM-05-S(K)36-9","doi-asserted-by":"crossref","unstructured":"9. Matsubara et al. also reported interesting H-D exchange reactions under hydrothermal conditions, see: (a) S. Matsubara, Y. Yokota, and K. Oshima, Chem. Lett., 2004, 33, 294. (b) S. Matsubara, Y. Yokota, and K. Oshima, Org. Lett., 2004, 6, 2071; (c) M. Yamamoto, Y. Yokota, K. Oshima, and S. Matsubara, Chem. Commun., 2004, 1714. (c) M. Yamamoto, K. Oshima, and S. Matsubara, Org. Lett., 2004, 6, 5015.","DOI":"10.1246\/cl.2004.294"},{"key":"10.3987\/COM-05-S(K)36-10","doi-asserted-by":"crossref","unstructured":"10. H. Sajiki, H. Esaki, F. Aoki, T. Maegawa, and K. Hirota, Synlett, 2005, 1385.","DOI":"10.1055\/s-2005-868489"},{"key":"10.3987\/COM-05-S(K)36-11","unstructured":"11. Although we previously reported10 that the glycosyl bond of thymidine completely was hydrolyzed under the same reaction conditions, we could obtain the deuterated thymidine at the 5-methyl group (71% deuterium efficiency) accompanied by the partial hydrolysis of thymidine."},{"key":"10.3987\/COM-05-S(K)36-12","doi-asserted-by":"crossref","unstructured":"12. No deuterium incorporation into the sugar moieties was found in all cases although Matsubara et al. recently reported quiet interesting H-D exchange reaction of primary alcohols at the \u03b1-position using RuCl2(PPh3)2 as a catalyst, see: M. Takahashi, K. Oshima, and S. Matsubara, Chem. Lett., 2005, 34, 192.","DOI":"10.1246\/cl.2005.192"},{"key":"10.3987\/COM-05-S(K)36-13","unstructured":"13. The Merck Index 13th Ed., Merck & CO., Inc., Whitehouse Station, 2001."}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T20:42:28Z","timestamp":1719261748000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-05-s%28k%2936"},"secondary":[{"URL":"https:\/\/triggered.edinburgh.clockss.org\/ServeContent?doi=10.3987%2Fcom-05-s%28k%2936","label":"edinburgh"}]},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005]]},"references-count":30,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2005]]}},"alternative-id":["COM-05-S(K)36"],"URL":"https:\/\/doi.org\/10.3987\/com-05-s(k)36","relation":{},"ISSN":["0385-5414"],"issn-type":[{"type":"print","value":"0385-5414"}],"subject":[],"published":{"date-parts":[[2005]]}}}