Synthesis of 2-Deoxyglycosides with Exclusive β-Configuration Using 2-SAc Glycosyl Bromide Donors
In this study, we developed an indirect method for the synthesis of 2-deoxyglycosides with an exclusive β-configuration using glucosyl and galactosyl bromide donors with 2-thioacetyl (SAc) groups. The 2-SAc glucosyl and galactosyl bromide donors were easily obtained through the treatment of 1-OAc, 2...
Saved in:
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-01-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/1/185 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Summary: | In this study, we developed an indirect method for the synthesis of 2-deoxyglycosides with an exclusive β-configuration using glucosyl and galactosyl bromide donors with 2-thioacetyl (SAc) groups. The 2-SAc glucosyl and galactosyl bromide donors were easily obtained through the treatment of 1-OAc, 2-SAc glucose and galactose with HBr-CH<sub>3</sub>COOH solution, respectively. The glycosylation of such donors with acceptors under an improved Koenigs–Knorr condition resulted in glycosylation products with an exclusive β-configuration in excellent yields. The synthetic approach of 2-SAc glycosyl donors using glycals as the starting materials was also investigated. Based on these studies, the synthetic method of using 2-deoxyglycosides with an exclusive β-configuration through desulfurization will have more practical applications. |
|---|---|
| ISSN: | 1420-3049 |