{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,24]],"date-time":"2026-08-24T09:29:58Z","timestamp":1787563798518,"version":"build-2736575974"},"reference-count":44,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2010,5,28]],"date-time":"2010-05-28T00:00:00Z","timestamp":1275004800000},"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":[[2010,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    In this report, we describe the stereoselective synthesis of a combinatorial library comprised of 16 deoxyhexasaccharides that are related to a landomycin A sugar moiety, based on an orthogonal deprotection strategy. The use of an olivosyl donor containing a benzyl ether at the C3 position and benzoyl ester at the C4 position, and the olivosyl donor, a naphthylmethyl ether, and a\n                    <jats:italic>p<\/jats:italic>\n                    \u2010nitrobenzylethyl or benzyl sulfonyl ester enabled the synthesis of a set of four diolivosyl units containing a hydroxyl group at the C3 or C4 position by a simple glycosylation and deprotection procedure. Using a phenylthio 2,3,6\u2010trideoxyglycoside, \u03b1\u2010selective glycosidation proceeded without anomerization of the 2,6\u2010dideoxy\u2010\u03b2\u2010glycosides. In addition, alkylhydroquinone and levulinoyl groups were found to be an effective set of orthogonal protecting groups for the anomeric position and a hydroxyl group. The coupling of all combinations of trisaccharide units in a \u03b2\u2010selective manner was accomplished by activation of the glycosyl imidate with I\n                    <jats:sub>2<\/jats:sub>\n                    and Et\n                    <jats:sub>3<\/jats:sub>\n                    SiH. No cleavage of the acid\u2010labile 2,3,6\u2010trideoxyglycoside was observed under the conditions used for the reactions. Finally, all of the protected hexasaccharides were deprotected by hydrolysis of the esters, microwave (MW) assisted cleavage of the 2\u2010trimethylsilylethoxymethoxy (SEM) ether, and a Birch reduction.\n                  <\/jats:p>","DOI":"10.1002\/asia.200900640","type":"journal-article","created":{"date-parts":[[2010,5,17]],"date-time":"2010-05-17T09:37:44Z","timestamp":1274089064000},"page":"1407-1424","source":"Crossref","is-referenced-by-count":40,"title":["Combinatorial Synthesis of Deoxyhexasaccharides Related to the Landomycin A Sugar Moiety, Based on an Orthogonal Deprotection Strategy"],"prefix":"10.1002","volume":"5","author":[{"given":"Hiroshi","family":"Tanaka","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sho","family":"Yamaguchi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Atsushi","family":"Yoshizawa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Motoki","family":"Takagi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazuo","family":"Shin\u2010ya","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takashi","family":"Takahashi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2010,5,28]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1007\/BFb0119234"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/np9971400099"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/np040106y"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-6976.2008.00124.x"},{"key":"e_1_2_6_6_2","unstructured":"\u00a0"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527618255.index"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00691-8"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00020a006"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200604031"},{"key":"e_1_2_6_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604031"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200800448"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980918)110:18<2620::AID-ANGE2620>3.0.CO;2-R"},{"key":"e_1_2_6_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19981002)37:18<2503::AID-ANIE2503>3.0.CO;2-R"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9813616"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)01690-1"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(99)00569-8"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(03)00553-7"},{"key":"e_1_2_6_18_2","unstructured":"\u00a0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.43.492"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/np9920900103"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00094a037"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1007\/BFb0119236"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/a702125i"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(99)00261-9"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200600360"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja973348b"},{"key":"e_1_2_6_27_2","unstructured":"\u00a0"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja000743k"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo015756a"},{"key":"e_1_2_6_30_2","unstructured":"\u00a0"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol006894"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0259286"},{"key":"e_1_2_6_33_2","unstructured":"Reports on the synthetic studies of landomycin oligosaccharides;"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0690(199811)1998:11<2267::AID-EJOC2267>3.0.CO;2-E"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800697k"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)93910-3"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2003.11.044"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)60378-7"},{"key":"e_1_2_6_39_2","unstructured":"Removal of the benzylethers on the deoxyhexasaccharides by hydrogenolysis using a palladium catalyst such as Pd\/C and Pd(OH)2failed. The 2 3 6\u2010trideoxyglycosides might be cleaved under the reaction conditions required."},{"key":"e_1_2_6_40_2","unstructured":"The cytotoxic effects of the 16 compounds2against three cancer cell lines (human cervical carcinoma HeLa cells human malignant pleural mesothelioma ACC\u2010MESO\u20101 cells16and human acute myelogenous leukemia HL\u201060 cells) were determined by WST\u20108 colorimetric assay kit (Dojindo Kumamoto Japan). These compounds did not show any cytotoxic effects even at a concentration of 50\u2005\u03bcMfor 48\u2005h."},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1349-7006.2006.00184.x"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802611w"}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fasia.200900640","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.200900640","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T16:25:49Z","timestamp":1759940749000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.200900640"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,5,28]]},"references-count":44,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2010,6]]}},"alternative-id":["10.1002\/asia.200900640"],"URL":"https:\/\/doi.org\/10.1002\/asia.200900640","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"value":"1861-4728","type":"print"},{"value":"1861-471X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2010,5,28]]}}}