{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,3]],"date-time":"2026-07-03T18:31:04Z","timestamp":1783103464423,"version":"3.54.6"},"reference-count":57,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2008,1,8]],"date-time":"2008-01-08T00:00:00Z","timestamp":1199750400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2008,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Glycosidation of a mannosyl donor in the presence of the Mukaiyama catalyst was found to give exceptionally high \u03b1\/\u03b2 selectivity. A systematic study was conducted to reveal that selective \u03b2\u2010to\u2010\u03b1 anomerization accounts for the observed high \u03b1\/\u03b2 stereoselectivity. Furthermore, the Mukaiyama catalyst was shown to exhibit an unusual level of substrate and anomer selectivity for the anomerization. On the basis of the combined anomeric and \u03942 effects, a mechanistic rationale was proposed, thereby suggesting the minimum structural moiety essential for the anomerization in question. With this analysis, \u03b2\u2010talo\u2010, \u03b2\u2010altro\u2010, and \u03b2\u2010idopyranosides are predicted to exhibit a reactivity profile similar to \u03b2\u2010mannopyranosides, but all other pyranosides should not. This prediction was verified by using \u03b2\u2010 and \u03b1\u2010talopyranosides as an example.<\/jats:p>","DOI":"10.1002\/asia.200700297","type":"journal-article","created":{"date-parts":[[2008,1,8]],"date-time":"2008-01-08T11:17:50Z","timestamp":1199791070000},"page":"319-326","source":"Crossref","is-referenced-by-count":15,"title":["Unique Reactivity of the Mukaiyama Glycosidation Catalyst (SnCl<sub>3<\/sub>ClO<sub>4<\/sub>) Toward \u03b2\u2010Mannopyranosides"],"prefix":"10.1002","volume":"3","author":[{"given":"Yonghui","family":"Wang","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hwan\u2010Sung","family":"Cheon","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yoshito","family":"Kishi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2008,1,29]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470122907.ch1"},{"key":"e_1_2_6_2_2","unstructured":"Isolation and characterization ofnMMPs:"},{"key":"e_1_2_6_3_2","doi-asserted-by":"crossref","first-page":"6835","DOI":"10.1016\/S0021-9258(19)45922-X","volume":"246","author":"Gary G. 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U.","year":"1964"},{"key":"e_1_2_6_27_2","first-page":"785","volume-title":"Glycoscience: Chemistry and Chemical Biology","author":"Koto S.","year":"2002"},{"key":"e_1_2_6_28_2","unstructured":"In the work onsMMP [3a]the experimental observations made suggested that the \u03b2\u2010to\u2010\u03b1 anomerization is virtually kinetically controlled for the reaction within 10\u2005h. However with longer reaction times the scrambled products were observed at least in the octasaccharide series thereby implying that formation of oxonium ion(s) from the \u03b1\u2005anomer is feasible although very sluggish."},{"key":"e_1_2_6_29_2","unstructured":"It is generally recognized that \u03b2\u2010mannosides are prone to facile anomerization.[6]"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1993.2145"},{"key":"e_1_2_6_31_2","unstructured":"A facile \u03b1\u2010to\u2010\u03b2 anomerization was observed for \u03b1\u2010mannopyranosides including mano\u2010\u03b1\u2010mano disaccharide10 in the presence of TiCl4(20\u2005mo\u2009%); for example allyl 3\u2010O\u2010methyl\u20102 4 6\u2010tri\u2010O\u2010benzyl\u2010\u03b1\u2010D\u2010mannopyranoside[3a]gave an approximately 94:6 mixture of \u03b1 and \u03b2\u2005anomers at room temperature in 5\u2005min in both CH2Cl2and Et2O."},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/0008-6215(93)84183-7"},{"key":"e_1_2_6_33_2","unstructured":"For a detailed analysis on the endocyclic and exocyclic cleavage of pyranoside acetals see for example:"},{"key":"e_1_2_6_34_2","unstructured":"reference\u2005[14a];"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja963807t"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1979.749"},{"key":"e_1_2_6_36_3","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.55.1092"},{"key":"e_1_2_6_36_4","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1997.625"},{"key":"e_1_2_6_36_5","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)74242-0"},{"key":"e_1_2_6_36_6","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)95447-9"},{"key":"e_1_2_6_36_7","doi-asserted-by":"publisher","DOI":"10.1351\/pac198860111705"},{"key":"e_1_2_6_36_8","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00120-3"},{"key":"e_1_2_6_36_9","doi-asserted-by":"publisher","DOI":"10.1016\/0008-6215(93)84183-7"},{"key":"e_1_2_6_36_10","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(98)00132-3"},{"key":"e_1_2_6_37_2","unstructured":"For monographs on this subject see:"},{"key":"e_1_2_6_38_2","volume-title":"Stereoelectronic Effects in Organic Chemistry","author":"Deslongchamps P.","year":"1983"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-68676-4"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01160a021"},{"key":"e_1_2_6_41_2","first-page":"49","volume-title":"Conformation of Carbohydrates","author":"Rao V. 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