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DOI: 10.1055/s-0036-1589501
Facile Approaches to 2-Deoxy-d-glucose and 2-Deoxy-α-d-glucopyranonucleosides from d-Glucal
Financial support from National Natural Science Foundation of China (21372207) is gratefully acknowledged.Publikationsverlauf
Received: 20. April 2017
Accepted after revision: 24. April 2017
Publikationsdatum:
07. Juni 2017 (online)
Abstract
Convenient and stereoselective methods for the preparation of 2-deoxy-d-glucose and purine 2-deoxy-α-d-glucopyranonucleosides were developed. Halogen-mediated O-glycosidation of d-glucal by bromine in MeOH followed by reductive removal of the halo group and hydrolysis of methoxy group by zinc in saturated aqueous sodium dihydrogen phosphate gave 2-deoxy-d-glucose. Treatment of 3,4,6-tri-O-acetyl-d-glucal with IBr and 2,6-dichloropurine based on haloetherification and subsequent reductive removal of iodine and deprotection allowed the isolation of purin-9-yl 2-deoxy-α-d-glucopyranonucleoside. Preparation of several purin-9-yl 2-deoxy-α-d-glucopyranoside derivatives is also reported. Their configuration was confirmed by single crystal X-ray analysis of the key intermediate 2,6-dichloro-9-(2-iodo-2-deoxy-α-d-glucopyranosyl)purine.
Key words
glucal - 2-deoxy-d-glucose - 2-deoxy-α-d-glucopyranonucleoside - halogen-mediated O-glycosidation - stereoselective synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589501.
- Supporting Information
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