{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,19]],"date-time":"2026-02-19T12:34:31Z","timestamp":1771504471856,"version":"3.50.1"},"reference-count":46,"publisher":"American Chemical Society (ACS)","issue":"4","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[2007,2,1]]},"DOI":"10.1021\/ol062887v","type":"journal-article","created":{"date-parts":[[2007,1,18]],"date-time":"2007-01-18T12:00:53Z","timestamp":1169121653000},"page":"623-626","source":"Crossref","is-referenced-by-count":26,"title":["Preliminary Studies on the Transformation of Nitrosugars into Branched Chain Iminosugars:\u2009 Synthesis of 1,4-Dideoxy-4-<i>C<\/i>-hydroxymethyl- 1,4-imino-pentanols"],"prefix":"10.1021","volume":"9","author":[{"given":"Jos\u00e9 M.","family":"Otero","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Universidade de Santiago, 15782 Santiago de Compostela, Spain, Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K., and Institute of Grassland and Environmental Research, Plas Goggerdan, Aberystwyth SY23 3EB, Wales, U.K."}]},{"given":"Raquel G.","family":"Soengas","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Universidade de Santiago, 15782 Santiago de Compostela, Spain, Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K., and Institute of Grassland and Environmental Research, Plas Goggerdan, Aberystwyth SY23 3EB, Wales, U.K."}]},{"given":"Juan C.","family":"Est\u00e9vez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Universidade de Santiago, 15782 Santiago de Compostela, Spain, Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K., and Institute of Grassland and Environmental Research, Plas Goggerdan, Aberystwyth SY23 3EB, Wales, U.K."}]},{"given":"Ram\u00f3n J.","family":"Est\u00e9vez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Universidade de Santiago, 15782 Santiago de Compostela, Spain, Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K., and Institute of Grassland and Environmental Research, Plas Goggerdan, Aberystwyth SY23 3EB, Wales, U.K."}]},{"given":"David J.","family":"Watkin","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Universidade de Santiago, 15782 Santiago de Compostela, Spain, Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K., and Institute of Grassland and Environmental Research, Plas Goggerdan, Aberystwyth SY23 3EB, Wales, U.K."}]},{"given":"Emma L.","family":"Evinson","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Universidade de Santiago, 15782 Santiago de Compostela, Spain, Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K., and Institute of Grassland and Environmental Research, Plas Goggerdan, Aberystwyth SY23 3EB, Wales, U.K."}]},{"given":"Robert J.","family":"Nash","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Universidade de Santiago, 15782 Santiago de Compostela, Spain, Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K., and Institute of Grassland and Environmental Research, Plas Goggerdan, Aberystwyth SY23 3EB, Wales, U.K."}]},{"given":"George W. J.","family":"Fleet","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Universidade de Santiago, 15782 Santiago de Compostela, Spain, Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K., and Institute of Grassland and Environmental Research, Plas Goggerdan, Aberystwyth SY23 3EB, Wales, U.K."}]}],"member":"316","published-online":{"date-parts":[[2007,1,18]]},"reference":[{"key":"ol062887vb00001\/ol062887vb00001_1","doi-asserted-by":"crossref","first-page":"3701","DOI":"10.1021\/jm00048a006","volume":"37","author":"Asano N.","year":"1994","journal-title":"J. Med. Chem."},{"key":"ol062887vb00002\/ol062887vb00002_1","doi-asserted-by":"crossref","unstructured":"(a) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J.Tetrahedron:\u2009 Asymmetry2000,11, 1645.","DOI":"10.1016\/S0957-4166(00)00113-0"},{"key":"ol062887vb00002\/ol062887vb00002_2","doi-asserted-by":"crossref","first-page":"1177","DOI":"10.2174\/1381612033454919","volume":"9","author":"Somsak L.","year":"2003","journal-title":"Curr. Pharm. Design"},{"key":"ol062887vb00003\/ol062887vb00003_1","doi-asserted-by":"crossref","first-page":"2903","DOI":"10.1002\/ejoc.200300163","volume":"15","author":"Ayad T.","year":"2003","journal-title":"Eur. J. Org. Chem."},{"key":"ol062887vb00003\/ol062887vb00003_2","doi-asserted-by":"crossref","first-page":"1305","DOI":"10.1055\/s-2000-6408","volume":"9","author":"Lee B. W.","year":"2000","journal-title":"Synthesis"},{"key":"ol062887vb00004\/ol062887vb00004_1","volume-title":"Wiley-VCH:\u2009 Weinheim","author":"Iminosugars","year":"1999"},{"key":"ol062887vb00005\/ol062887vb00005_1","unstructured":"(a) Fleet, G. W. J.; Witty, D. R.Tetrahedron:\u2009 Asymmetry1990,1, 119."},{"key":"ol062887vb00005\/ol062887vb00005_2","doi-asserted-by":"crossref","first-page":"3359","DOI":"10.1016\/S0040-4020(01)90163-2","volume":"49","author":"Behling J. R.","year":"1993","journal-title":"J. Tetrahedron"},{"key":"ol062887vb00005\/ol062887vb00005_3","doi-asserted-by":"crossref","first-page":"3127","DOI":"10.1016\/S0040-4039(00)98636-2","volume":"26","author":"Fleet G. W. J.","year":"1985","journal-title":"J. Tetrahedron Lett."},{"key":"ol062887vb00006\/ol062887vb00006_1","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1016\/S0006-291X(03)00540-0","volume":"304","author":"Mizushina Y.","year":"2003","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ol062887vb00007\/ol062887vb00007_1","doi-asserted-by":"crossref","first-page":"3021","DOI":"10.1021\/ol0609210","volume":"8","author":"Yu C.-Y.","year":"2006","journal-title":"Org. Lett."},{"key":"ol062887vb00007\/ol062887vb00007_2","doi-asserted-by":"crossref","first-page":"525","DOI":"10.2174\/1568026033452465","volume":"3","author":"Schramm V. L.","year":"2003","journal-title":"Curr. Top. Med. Chem."},{"key":"ol062887vb00007\/ol062887vb00007_3","doi-asserted-by":"crossref","first-page":"7126","DOI":"10.1021\/ja061403n","volume":"128","author":"Ringia E. A. T.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ol062887vb00008\/ol062887vb00008_1","first-page":"1936","volume":"17","author":"Yu C.-Y.","year":"2004","journal-title":"J. Chem. Commun."},{"key":"ol062887vb00009\/ol062887vb00009_1","doi-asserted-by":"crossref","first-page":"3411","DOI":"10.1021\/jo980078m","volume":"63","author":"For","year":"1998","journal-title":"J. Org. Chem."},{"key":"ol062887vb00010\/ol062887vb00010_1","doi-asserted-by":"crossref","first-page":"2649","DOI":"10.1016\/S0040-4020(01)81717-8","volume":"44","author":"Fleet G. W. J.","year":"1988","journal-title":"Tetrahedron"},{"key":"ol062887vb00011\/ol062887vb00011_1","doi-asserted-by":"crossref","first-page":"1131","DOI":"10.1039\/b517883e","volume":"4","author":"Clinch K.","year":"2006","journal-title":"Org. Biomol. Chem."},{"key":"ol062887vb00012\/ol062887vb00012_1","doi-asserted-by":"crossref","first-page":"751","DOI":"10.1021\/cr00075a002","volume":"86","author":"Barret A. G. M.","year":"1986","journal-title":"Chem. Rev."},{"key":"ol062887vb00012\/ol062887vb00012_2","unstructured":"(b)Nitroalkanes and Nitroalkenes in Synthesis; Tetrahedron Symposia; Barret, A. G. M., Ed.; 1990; Vol. 46, p 7313."},{"key":"ol062887vb00012\/ol062887vb00012_3","series-title":"Organic Nitro Chemistry Series","volume-title":"In The Nitro Group in Organic Synthesis","author":"Noboru O.","year":"2001"},{"key":"ol062887vb00013\/ol062887vb00013_1","doi-asserted-by":"crossref","first-page":"915","DOI":"10.1016\/S0040-4020(00)00965-0","volume":"57","author":"Luzzio F. A.","year":"2001","journal-title":"Tetrahedron"},{"key":"ol062887vb00014\/ol062887vb00014_1","first-page":"655","volume":"38","author":"Pinnick H. W.","year":"1990","journal-title":"Org. React."},{"key":"ol062887vb00014\/ol062887vb00014_2","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1021\/jo00916a037","volume":"39","author":"McMurry J. E.","year":"1974","journal-title":"J. Org. Chem."},{"key":"ol062887vb00014\/ol062887vb00014_3","doi-asserted-by":"crossref","first-page":"4367","DOI":"10.1021\/jo00965a004","volume":"38","author":"McMurry J. E.","year":"1973","journal-title":"J. Org. Chem."},{"key":"ol062887vb00015\/ol062887vb00015_1","unstructured":"(a) Otero, J. M.; Fern\u00e1ndez, F.; Est\u00e9vez, J. C.; Est\u00e9vez, R. J.Tetrahedron:\u2009 Asymmetry2005,16, 4045."},{"key":"ol062887vb00015\/ol062887vb00015_2","unstructured":"(b) Otero, J. M.; Barcia, J. C.; Est\u00e9vez, J. C.; Est\u00e9vez, R. J.Tetrahedron:\u2009 Asymmetry2005,16, 11."},{"key":"ol062887vb00015\/ol062887vb00015_3","unstructured":"(c) Soengas, R. G.; Pamp\u00edn, M. B.; Est\u00e9vez, J. C.; Est\u00e9vez, R. J.Tetrahedron:\u2009Asymmetry2005,15, 211."},{"key":"ol062887vb00015\/ol062887vb00015_4","doi-asserted-by":"crossref","unstructured":"(d) Soengas, R. G.; Est\u00e9vez, J. C.; Est\u00e9vez, R. J.Tetrahedron:\u2009 Asymmetry2003,14, 3955.","DOI":"10.1016\/S0957-4166(03)00274-X"},{"key":"ol062887vb00015\/ol062887vb00015_5","doi-asserted-by":"crossref","first-page":"4457","DOI":"10.1021\/ol035771x","volume":"5","author":"Soengas R. G.","year":"2003","journal-title":"J. Org. Lett."},{"key":"ol062887vb00015\/ol062887vb00015_6","doi-asserted-by":"crossref","unstructured":"(f) Soengas, R. G.; Est\u00e9vez, J. C.; Est\u00e9vez, R. J.; Maestro, M. A.Tetrahedron:\u2009 Asymmetry2003,14, 1653.","DOI":"10.1016\/S0957-4166(03)00274-X"},{"key":"ol062887vb00015\/ol062887vb00015_7","doi-asserted-by":"crossref","first-page":"1423","DOI":"10.1021\/ol034127f","volume":"5","author":"Soengas R. G.","year":"2003","journal-title":"J. Org. Lett."},{"key":"ol062887vb00016\/ol062887vb00016_1","first-page":"152","volume":"33","author":"Choudary B. M.","year":"1994","journal-title":"Indian J. Chem."},{"key":"ol062887vb00016\/ol062887vb00016_2","doi-asserted-by":"crossref","first-page":"976","DOI":"10.1021\/bi00895a023","volume":"3","author":"LeCocq J.","year":"1964","journal-title":"Biochemistry"},{"key":"ol062887vb00016\/ol062887vb00016_3","doi-asserted-by":"crossref","first-page":"1460","DOI":"10.1039\/C39830001460","volume":"23","author":"Kozikowski A. P.","year":"1983","journal-title":"J. Chem. Soc., Chem. Commun."},{"key":"ol062887vb00017\/ol062887vb00017_1","volume-title":"Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road","author":"Crystallographic"},{"key":"ol062887vb00018\/ol062887vb00018_1","first-page":"3409","author":"Schieweck F.","year":"2001","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"ol062887vb00019\/ol062887vb00019_1","doi-asserted-by":"crossref","first-page":"1547","DOI":"10.1016\/0040-4039(96)00068-8","volume":"37","author":"Sun L.","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"ol062887vb00020\/ol062887vb00020_1","doi-asserted-by":"crossref","first-page":"296","DOI":"10.7164\/antibiotics.41.296","volume":"41","author":"Shibata T.","year":"1988","journal-title":"J. Antibiot."},{"key":"ol062887vb00020\/ol062887vb00020_2","doi-asserted-by":"crossref","first-page":"1725","DOI":"10.1016\/S0040-4039(00)82028-6","volume":"29","author":"Kayakiri H.","year":"1988","journal-title":"Tetrahedron Lett."},{"key":"ol062887vb00020\/ol062887vb00020_3","doi-asserted-by":"crossref","first-page":"459","DOI":"10.1006\/bbrc.1996.0427","volume":"220","author":"Tsujii E.","year":"1996","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ol062887vb00021\/ol062887vb00021_1","doi-asserted-by":"crossref","first-page":"5724","DOI":"10.1021\/jo00071a045","volume":"58","author":"Cicchi S.","year":"1993","journal-title":"J. Org. Chem."},{"key":"ol062887vb00022\/ol062887vb00022_1","doi-asserted-by":"crossref","first-page":"647","DOI":"10.1002\/cber.19901230336","volume":"123","author":"Balicki R.","year":"1990","journal-title":"Chem. Ber."},{"key":"ol062887vb00023\/ol062887vb00023_1","first-page":"1366","author":"Acidic","year":"2000","journal-title":"Synlett"},{"key":"ol062887vb00024\/ol062887vb00024_1","doi-asserted-by":"crossref","first-page":"5091","DOI":"10.1016\/j.bmc.2004.07.039","volume":"12","author":"Tite T.","year":"2004","journal-title":"Bioorg. Med. Chem."},{"key":"ol062887vb00025\/ol062887vb00025_1","doi-asserted-by":"crossref","first-page":"1269","DOI":"10.1016\/S0968-0896(00)00343-6","volume":"9","author":"Martin O. L.","year":"2001","journal-title":"Bioorg. Med. Chem."},{"key":"ol062887vb00026\/ol062887vb00026_1","doi-asserted-by":"crossref","first-page":"1653","DOI":"10.1039\/B518117H","volume":"4","author":"Li H.","year":"2006","journal-title":"Org. Biomol. Chem."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol062887v","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,6]],"date-time":"2023-04-06T16:15:00Z","timestamp":1680797700000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol062887v"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007,1,18]]},"references-count":46,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2007,2,1]]}},"alternative-id":["10.1021\/ol062887v"],"URL":"https:\/\/doi.org\/10.1021\/ol062887v","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2007,1,18]]}}}