Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranoside: isolation, crystal structure and conformation

Eleanor Dodd; Simon J. Coles; William Fraser

doi:10.1016/j.carres.2026.109831

Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranoside: isolation, crystal structure and conformation

Eleanor Dodd^*, Simon J. Coles, William Fraser^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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 I2. 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 0E (O4-endo) with P = 89.9° and φm = 64.4°.

Original language	English
Article number	109831
Number of pages	4
Journal	Carbohydrate Research
Volume	562
Early online date	16 Jan 2026
DOIs	https://doi.org/10.1016/j.carres.2026.109831
Publication status	E-pub ahead of print - 16 Jan 2026

Bibliographical note

Data Access Statement

Crystallographic data were deposited at CSD (CIF deposition number; 2503002).

Funding

The authors thank the Royal Society of Chemistry for a Research Fund Grant (R23-2829172975) and Prof. Zaid Alobaidi (Aston University) for mass analysis.

Keywords

Alpha anomer
Conformation
Crystal structure
Hoffer chlorosugar
Methyl glycoside
Nucleoside

Access to Document

10.1016/j.carres.2026.109831Licence: CC BY 4.0

Dodd Coles and Fraser_Methyl 2-deoxy-3_5-di-O-p-toluoyl-alpha-D-ribofuranoside_isolation crystal structure and conformation
Copyright © 2026 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (https://creativecommons.org/licenses/by/4.0/).
Final published version, 1.83 MBLicence: CC BY 4.0

Cite this

@article{27ac4668984f48acbf9cf73e472f7f27,

title = "Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranoside: isolation, crystal structure and conformation",

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 I2. Methyl glycoside (5) possesses a glycosidic bond length of 1.408 {\AA} with pseudorotational analysis showing the conformation of the five-membered ring to be 0E (O4-endo) with P = 89.9° and φm = 64.4°.",

keywords = "Alpha anomer, Conformation, Crystal structure, Hoffer chlorosugar, Methyl glycoside, Nucleoside",

author = "Eleanor Dodd and Coles, {Simon J.} and William Fraser",

note = "Copyright {\textcopyright} 2026 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (https://creativecommons.org/licenses/by/4.0/).",

year = "2026",

month = jan,

day = "16",

doi = "10.1016/j.carres.2026.109831",

language = "English",

volume = "562",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier",

}

TY - JOUR

T1 - Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranoside: isolation, crystal structure and conformation

AU - Dodd, Eleanor

AU - Coles, Simon J.

AU - Fraser, William

PY - 2026/1/16

Y1 - 2026/1/16

N2 - 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 I2. 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 0E (O4-endo) with P = 89.9° and φm = 64.4°.

AB - 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 I2. 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 0E (O4-endo) with P = 89.9° and φm = 64.4°.

KW - Alpha anomer

KW - Conformation

KW - Crystal structure

KW - Hoffer chlorosugar

KW - Methyl glycoside

KW - Nucleoside

UR - https://linkinghub.elsevier.com/retrieve/pii/S0008621526000200

UR - http://www.scopus.com/inward/record.url?scp=105027379239&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2026.109831

DO - 10.1016/j.carres.2026.109831

M3 - Article

SN - 0008-6215

VL - 562

JO - Carbohydrate Research

JF - Carbohydrate Research

M1 - 109831

ER -

Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranoside: isolation, crystal structure and conformation

Abstract

Bibliographical note

Data Access Statement

Funding

Keywords

Access to Document

Other files and links

Fingerprint

Cite this