Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranoside: isolation, crystal structure and conformation
Year: 2026
Type: article
Abstract: The X-ray crystal structure of methyl 2-deoxy-3,5- di - O - p -toluoyl- α - d -ribofuranoside ( 5 ) presented here, is a unique example of an alpha-configured, methyl 2-deoxyribofuranoside with the same protecting group at positions C3 and C5. Methyl 2-deoxy-3,5- di - O - p -toluoyl- α/β - d -ribofuranoside ( 3 ), exists as a mixture of alpha and beta anomers from which we isolated a single anomer on recrystallization from acetone. TLC analysis indicated the presence of a single compound with NMR analysis in support of the alpha anomer. SC-XRD analysis showed that methyl glycoside ( 5 ) crystallizes from acetone as the alpha anomer in the monoclinic space group I 2. Methyl glycoside ( 5 ) possesses a glycosidic bond length of 1.408 Å with pseudorotational analysis showing the conformation of the five-membered ring to be 0 E (O4- endo ) with P = 89.9° and φ m = 64.4°. • Anomer-selective crystallization of methyl glycoside ( 3 ). Crystal structure of the first alpha methyl glycoside with the same protecting group at C3 and C5. Selection of the alpha anomer assisted by the anomeric effect.
Source: Carbohydrate Research
Authors: Eleanor Dodd, Simon J. Coles, William Fraser
Institutions: University of Southampton, Aston University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $3,800
Award: G1394454486
OpenAlex ID: W7124444144