Boronic Acid-Catalyzed Regioselective Koenigs–Knorr-Type Glycosylation
Boronic acid-catalyzed regioselective Koenigs–Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proce...
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| Published in | Journal of organic chemistry Vol. 86; no. 8; pp. 5973 - 5982 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
16.04.2021
Amer Chemical Soc |
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| Abstract | Boronic acid-catalyzed regioselective Koenigs–Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proceed smoothly, which enables construction of a 1,2-trans glycosidic linkage with high regioselectivities. This is the first example of the use of a boronic acid catalyst to initiate regioselective glycosylation via the activation of cis-vicinal diols in glycosyl acceptors. |
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| AbstractList | Boronic acid-catalyzed regioselective Koenigs-Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proceed smoothly, which enables construction of a 1,2-trans glycosidic linkage with high regioselectivities. This is the first example of the use of a boronic acid catalyst to initiate regioselective glycosylation via the activation of cis-vicinal diols in glycosyl acceptors. Boronic acid-catalyzed regioselective Koenigs-Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proceed smoothly, which enables construction of a 1,2- glycosidic linkage with high regioselectivities. This is the first example of the use of a boronic acid catalyst to initiate regioselective glycosylation via the activation of -vicinal diols in glycosyl acceptors. Boronic acid-catalyzed regioselective Koenigs-Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proceed smoothly, which enables construction of a 1,2-trans glycosidic linkage with high regioselectivities. This is the first example of the use of a boronic acid catalyst to initiate regioselective glycosylation via the activation of cis-vicinal diols in glycosyl acceptors.Boronic acid-catalyzed regioselective Koenigs-Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proceed smoothly, which enables construction of a 1,2-trans glycosidic linkage with high regioselectivities. This is the first example of the use of a boronic acid catalyst to initiate regioselective glycosylation via the activation of cis-vicinal diols in glycosyl acceptors. |
| Author | Noguchi, Mao Takahashi, Naoya Kuwashima, Yutaro Sato, Noriko Sugimoto, Tomoya Makino, Kazuishi Ohira, Chikako Shimada, Naoyuki |
| AuthorAffiliation | Laboratory of Organic Chemistry for Drug Development and Medical Research Laboratories, Department of Pharmaceutical Sciences |
| AuthorAffiliation_xml | – name: Laboratory of Organic Chemistry for Drug Development and Medical Research Laboratories, Department of Pharmaceutical Sciences |
| Author_xml | – sequence: 1 givenname: Naoyuki orcidid: 0000-0002-0143-7867 surname: Shimada fullname: Shimada, Naoyuki email: shimadan@pharm.kitasato-u.ac.jp – sequence: 2 givenname: Tomoya surname: Sugimoto fullname: Sugimoto, Tomoya – sequence: 3 givenname: Mao surname: Noguchi fullname: Noguchi, Mao – sequence: 4 givenname: Chikako surname: Ohira fullname: Ohira, Chikako – sequence: 5 givenname: Yutaro surname: Kuwashima fullname: Kuwashima, Yutaro – sequence: 6 givenname: Naoya surname: Takahashi fullname: Takahashi, Naoya – sequence: 7 givenname: Noriko surname: Sato fullname: Sato, Noriko – sequence: 8 givenname: Kazuishi orcidid: 0000-0001-8518-6593 surname: Makino fullname: Makino, Kazuishi |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33829786$$D View this record in MEDLINE/PubMed |
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| Keywords | TRANSIENT MASKING ACTIVATION OLIGOSACCHARIDES ACYLATION NATURAL-PRODUCTS ALKYLATION HEXOPYRANOSIDE GLYCOSIDATIONS SILYLATION CARBOHYDRATE-CHEMISTRY |
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| Snippet | Boronic acid-catalyzed regioselective Koenigs–Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor... Boronic acid-catalyzed regioselective Koenigs-Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor... |
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| SubjectTerms | boronic acids catalysts Chemistry Chemistry, Organic glycols glycosidic linkages glycosylation organic chemistry Physical Sciences regioselectivity Science & Technology silver oxide |
| Title | Boronic Acid-Catalyzed Regioselective Koenigs–Knorr-Type Glycosylation |
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