{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:44:18Z","timestamp":1760143458848,"version":"build-2065373602"},"reference-count":48,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2024,2,9]],"date-time":"2024-02-09T00:00:00Z","timestamp":1707436800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"CONACYT Mexico","award":["286620","509229"],"award-info":[{"award-number":["286620","509229"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>We synthesized six new camphor-derived homochiral thioureas 1\u20136, from commercially available (1R)-(\u2212)-camphorquinone. These new compounds 1\u20136 were evaluated as asymmetric organocatalysts in the stereoselective formation of glycosidic bonds, with 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl and 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetimidates as donors, and several alcohols as glycosyl acceptors, such as methanol, ethanol, 1-propanol, 1-butanol, 1-octanol, iso-propanol, tert-butanol, cyclohexanol, phenol, 1-naphtol, and 2-naphtol. Optimization of the asymmetric glycosylation reaction was achieved by modifying reaction conditions such as solvent, additive, loading of catalyst, temperature, and time of reaction. The best result was obtained with 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetimidates, using 15 mol% of organocatalyst 1, in the presence of 2 equiv of MeOH in solvent-free conditions at room temperature for 1.5 h, affording the glycosidic compound in a 99% yield and 1:73 \u03b1:\u03b2 stereoselectivity; under the same reaction conditions, without using a catalyst, the obtained stereoselectivity was 1:35 \u03b1:\u03b2. Computational calculations prior to the formation of the products were modeled, using density functional theory, M06-2X\/6-31G(d,p) and M06-2X\/6-311++G(2d,2p) methods. We observed that the preference for \u03b2 glycoside formation, through a stereoselective inverted substitution, relies on steric effects and the formation of hydrogen bonds between thiourea 1 and methanol in the complex formed.<\/jats:p>","DOI":"10.3390\/molecules29040811","type":"journal-article","created":{"date-parts":[[2024,2,9]],"date-time":"2024-02-09T11:42:05Z","timestamp":1707478925000},"page":"811","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Use of Novel Homochiral Thioureas Camphor Derived as Asymmetric Organocatalysts in the Stereoselective Formation of Glycosidic Bonds"],"prefix":"10.3390","volume":"29","author":[{"given":"Mildred","family":"L\u00f3pez","sequence":"first","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmico-Biol\u00f3gicas, Universidad de las Am\u00e9ricas Puebla, Puebla 72810, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gabriela","family":"Huelgas","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmico-Biol\u00f3gicas, Universidad de las Am\u00e9ricas Puebla, Puebla 72810, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1458-2270","authenticated-orcid":false,"given":"Mario","family":"S\u00e1nchez","sequence":"additional","affiliation":[{"name":"Centro de Investigaci\u00f3n en Materiales Avanzados S.C., Alianza Norte 202, PIIT, Apodaca 66628, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Adalid","family":"Armenta","sequence":"additional","affiliation":[{"name":"Centro de Investigaci\u00f3n en Materiales Avanzados S.C., Alianza Norte 202, PIIT, Apodaca 66628, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0760-9084","authenticated-orcid":false,"given":"Angel","family":"Mendoza","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica, Instituto de Ciencias, Benem\u00e9rita Universidad Aut\u00f3noma de Puebla, Puebla 72570, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6556-5833","authenticated-orcid":false,"given":"Jos\u00e9 Daniel","family":"Lozada-Ram\u00edrez","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmico-Biol\u00f3gicas, Universidad de las Am\u00e9ricas Puebla, Puebla 72810, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cecilia","family":"Anaya de Parrodi","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmico-Biol\u00f3gicas, Universidad de las Am\u00e9ricas Puebla, Puebla 72810, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,2,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1121","DOI":"10.1055\/s-0036-1588722","article-title":"2,6-Lactones as a New Entry in Stereoselective Glycosylations","volume":"28","author":"Sasaki","year":"2017","journal-title":"Synlett"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"8242","DOI":"10.1021\/acs.chemrev.8b00083","article-title":"The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1\u2013SN2 Interface","volume":"118","author":"Adero","year":"2018","journal-title":"Chem. 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