Reactivity, Selectivity, and Synthesis of 4‐C‐Silylated Glycosyl Donors and 4‐Deoxy Analogues
A method for introducing dimethylphenylsilyl at the 4‐position in carbohydrates has been developed. Two C‐silylated glycosyl donors were prepared via levoglucosenone, starting from cellulose. The glycosylation properties were studied using three glucoside acceptors, a 3‐OH, 4‐OH, and 6‐OH. Compared...
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| Published in | Angewandte Chemie International Edition Vol. 60; no. 5; pp. 2689 - 2693 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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Wiley
01.02.2021
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| Edition | International ed. in English |
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| Abstract | A method for introducing dimethylphenylsilyl at the 4‐position in carbohydrates has been developed. Two C‐silylated glycosyl donors were prepared via levoglucosenone, starting from cellulose. The glycosylation properties were studied using three glucoside acceptors, a 3‐OH, 4‐OH, and 6‐OH. Compared with the 4‐deoxy variant, it was found that the anomeric selectivity was influenced more by the C‐2 substituents orientation than the silyl in the 4‐position. In general, the reactivity of these donors was higher than the corresponding 4‐deoxy‐analogue, albeit a competition experiment showed that the introduction of a C−Si increases the relative reactivity by a modest factor of around two.
Two 4‐C‐silylated glycosyl donors have been synthesized starting from cellulose. This new class of donors showed remarkably similar selectivity to and modestly more reactivity than their 4‐C‐deoxy analogue, allowing for very mild glycosylation reaction conditions and short reaction times. |
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| AbstractList | Abstract
A method for introducing dimethylphenylsilyl at the 4‐position in carbohydrates has been developed. Two C‐silylated glycosyl donors were prepared via levoglucosenone, starting from cellulose. The glycosylation properties were studied using three glucoside acceptors, a 3‐OH, 4‐OH, and 6‐OH. Compared with the 4‐deoxy variant, it was found that the anomeric selectivity was influenced more by the C‐2 substituents orientation than the silyl in the 4‐position. In general, the reactivity of these donors was higher than the corresponding 4‐deoxy‐analogue, albeit a competition experiment showed that the introduction of a C−Si increases the relative reactivity by a modest factor of around two. A method for introducing dimethylphenylsilyl at the 4-position in carbohydrates has been developed. Two C-silylated glycosyl donors were prepared via levoglucosenone, starting from cellulose. The glycosylation properties were studied using three glucoside acceptors, a 3-OH, 4-OH, and 6-OH. Compared with the 4-deoxy variant, it was found that the anomeric selectivity was influenced more by the C-2 substituents orientation than the silyl in the 4-position. In general, the reactivity of these donors was higher than the corresponding 4-deoxy-analogue, albeit a competition experiment showed that the introduction of a C-Si increases the relative reactivity by a modest factor of around two. A method for introducing dimethylphenylsilyl at the 4‐position in carbohydrates has been developed. Two C‐silylated glycosyl donors were prepared via levoglucosenone, starting from cellulose. The glycosylation properties were studied using three glucoside acceptors, a 3‐OH, 4‐OH, and 6‐OH. Compared with the 4‐deoxy variant, it was found that the anomeric selectivity was influenced more by the C‐2 substituents orientation than the silyl in the 4‐position. In general, the reactivity of these donors was higher than the corresponding 4‐deoxy‐analogue, albeit a competition experiment showed that the introduction of a C−Si increases the relative reactivity by a modest factor of around two. A method for introducing dimethylphenylsilyl at the 4‐position in carbohydrates has been developed. Two C‐silylated glycosyl donors were prepared via levoglucosenone, starting from cellulose. The glycosylation properties were studied using three glucoside acceptors, a 3‐OH, 4‐OH, and 6‐OH. Compared with the 4‐deoxy variant, it was found that the anomeric selectivity was influenced more by the C‐2 substituents orientation than the silyl in the 4‐position. In general, the reactivity of these donors was higher than the corresponding 4‐deoxy‐analogue, albeit a competition experiment showed that the introduction of a C−Si increases the relative reactivity by a modest factor of around two. Two 4‐C‐silylated glycosyl donors have been synthesized starting from cellulose. This new class of donors showed remarkably similar selectivity to and modestly more reactivity than their 4‐C‐deoxy analogue, allowing for very mild glycosylation reaction conditions and short reaction times. |
| Author | Pedersen, Christian Marcus Jæger Pedersen, Martin |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33025650$$D View this record in MEDLINE/PubMed |
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| Keywords | selectivity synthesis OXIDATION 1,2-SILYL-MIGRATIVE CYCLIZATION ACID glycosylation ALPHA BETA silylation CARBON BOND VINYLSILANES BEARING CHEMISTRY ORGANOSILICON COMPOUNDS levoglucosenone CONFORMATIONAL PREFERENCE |
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| Snippet | A method for introducing dimethylphenylsilyl at the 4‐position in carbohydrates has been developed. Two C‐silylated glycosyl donors were prepared via... A method for introducing dimethylphenylsilyl at the 4-position in carbohydrates has been developed. Two C-silylated glycosyl donors were prepared via... Abstract A method for introducing dimethylphenylsilyl at the 4‐position in carbohydrates has been developed. Two C‐silylated glycosyl donors were prepared via... |
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| SubjectTerms | Carbohydrates Cellulose Chemistry Chemistry, Multidisciplinary Glycosylation levoglucosenone Physical Sciences Reactivity Science & Technology Selectivity silylation synthesis |
| Title | Reactivity, Selectivity, and Synthesis of 4‐C‐Silylated Glycosyl Donors and 4‐Deoxy Analogues |
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