{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,15]],"date-time":"2026-01-15T02:14:16Z","timestamp":1768443256773,"version":"3.49.0"},"reference-count":14,"publisher":"American Chemical Society (ACS)","issue":"2","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[1999,7,1]]},"DOI":"10.1021\/ol9905811","type":"journal-article","created":{"date-parts":[[2002,7,26]],"date-time":"2002-07-26T05:45:00Z","timestamp":1027662300000},"page":"245-248","source":"Crossref","is-referenced-by-count":36,"title":["Synthesis of \u03b2-<scp>d<\/scp>-Gal<i>f<\/i>-(1\u22123)-<scp>d<\/scp>-GlcNAc by the Trichloroacetamidate Method and of \u03b2-<scp>d<\/scp>-Gal<i>f<\/i>-(1\u22126)-<scp>d<\/scp>-GlcNAc by SnCl<sub>4<\/sub>-Promoted Glycosylation"],"prefix":"10.1021","volume":"1","author":[{"given":"Carola","family":"Gallo-Rodriguez","sequence":"first","affiliation":[{"name":"CIHIDECAR, Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, Buenos Aires 1428, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lucia","family":"Gandolfi","sequence":"additional","affiliation":[{"name":"CIHIDECAR, Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, Buenos Aires 1428, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rosa M.","family":"de Lederkremer","sequence":"additional","affiliation":[{"name":"CIHIDECAR, Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, Buenos Aires 1428, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"316","published-online":{"date-parts":[[1999,5,27]]},"reference":[{"key":"ol9905811b00001\/ol9905811b00001_1","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1042\/bj3010151","volume":"301","author":"Previato J. O.","year":"1994","journal-title":"Biochem. J."},{"key":"ol9905811b00001\/ol9905811b00001_2","doi-asserted-by":"crossref","first-page":"27244","DOI":"10.1074\/jbc.270.45.27244","volume":"270","author":"Acosta Serrano A.","year":"1995","journal-title":"J. Biol. Chem."},{"key":"ol9905811b00002\/ol9905811b00002_1","doi-asserted-by":"crossref","first-page":"1886","DOI":"10.1021\/jo951934m","volume":"61","author":"Gallo-Rodriguez C.","year":"1996","journal-title":"J. Org. Chem."},{"key":"ol9905811b00003\/ol9905811b00003_1","doi-asserted-by":"crossref","first-page":"7241","DOI":"10.1074\/jbc.270.13.7241","volume":"270","author":"Previato J. O.","year":"1995","journal-title":"J. Biol. Chem."},{"key":"ol9905811b00004\/ol9905811b00004_1","first-page":"20","volume-title":"Modern Methods in Carbohydrate Synthesis","author":"Schmidt R.","year":"1996"},{"key":"ol9905811b00004\/ol9905811b00004_2","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1016\/S0065-2318(08)60150-X","volume":"50","author":"Schmidt R. R.","year":"1994","journal-title":"Adv. Carbohydr. Chem. Biochem."},{"key":"ol9905811b00005\/ol9905811b00005_1","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1016\/S0008-6215(98)00062-7","volume":"308","author":"Choudhury A. K.","year":"1998","journal-title":"Carbohydr. Res."},{"key":"ol9905811b00006\/ol9905811b00006_1","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/0008-6215(89)84147-3","volume":"190","author":"Marino C.","year":"1989","journal-title":"Carbohydr. 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To a solution of acetamidate6(700 mg, 0.94 mmol) in dry Cl2CH2(30 mL) and CH3CN (1 mL) were added anhydrous benzyl 2-acetamido\u22124,6-O-benzylidene-2-deoxy\u2212\u03b1-d-glucopyranoside (3; 360 mg, 0.90 mmol) and 4 \u00c5 powder molecular sieves. The suspension was vigorously stirred for 5 min at room temperature under Ar and then cooled to \u221220 \u00b0C. TMSOTf was added (150 \u03bcL, 0.83 mmol) and the stirring continued for 1 h. After the mixture was warmed to room temperature, solid NaHCO3(200 mg) was added with vigorous stirring and the suspension was filtered over Celite. The filtrate was diluted with Cl2CH2(150 mL), washed with water (3 \u00d7 100 mL), dried (MgSO4), filtered, and concentrated. Purification of the residue by silica gel column chromatography (10:1 toluene-EtOAc) yielded7(720 mg, 82%) as a foamy solid. Unreacted3was also recovered (52 mg, 14%). Compound7:\u2009Rf0.56, 2:1 toluene\u2212EtOAc; [\u03b1]D+32.6\u00b0 (c= 1, CHCl3);1H NMR (200 MHz, CDCl3) \u03b4 8.1\u22127.1 (m, 30H), 5.86 (dt, 1H,J= 8.8, 2.9 Hz, H-5\u2018), 5.80 (d, 1H,J= 9.5 Hz, NH), 5.48 (d, 1H,J= 4.8 Hz, H-3\u2018), 5.41 , 5.40 (2s, 2H, H-1\u2018, PhCH), 5.33 (br s, 1H, H-2\u2018), 4.93 (d, 1H,J= 3.7 Hz, H-1), 4.77, 4.51 (2d, 2H,J= 11.7 Hz, PhCH2), 4.62 (dd, 1H,J= 4.8, 2.9 Hz, H-4\u2018), 4.51 (m, 1H, H-2), 4.45 (t, 1H,J= 8.8 Hz, H\u22126\u2018a), 4.26 (dd, 1H,J= 10.2, 4.4 Hz, H\u22126a), 4.09 (t, 1H,J= 9.7 Hz, H-3), 3.96 (m, 1H, H-5), 3.90 (dd, 1H,J= 8.8, 2.9 Hz, H-6\u2018b), 3.73 (t, 1H,J= 10.2 Hz, H-6b), 3.67 (t, 1H,J= 9.1 Hz, H-4), 1.98 (s, 3H, CH3). A 2D-COSY1H NMR correlation spectrum allowed the assigment of the1H signals. Anal. Calcd for C56H51NO15:\u2009 C, 68.77; H, 5.26. Found:\u2009 C, 68.76; H, 5.22."},{"key":"ol9905811b00011\/ol9905811b00011_1","volume-title":"To an externally cooled (0 \u00b0C) solution of 1,2,3,5,6-penta-O-benzoyl-\u03b1,\u03b2-d-galactofuranose7 (4","author":"Procedure"}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol9905811","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,10,17]],"date-time":"2021-10-17T12:06:45Z","timestamp":1634472405000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol9905811"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1999,5,27]]},"references-count":14,"journal-issue":{"issue":"2","published-print":{"date-parts":[[1999,7,1]]}},"alternative-id":["10.1021\/ol9905811"],"URL":"https:\/\/doi.org\/10.1021\/ol9905811","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[1999,5,27]]}}}