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Synthesis 2017; 49(16): 3686-3691
DOI: 10.1055/s-0036-1589501
paper
© Georg Thieme Verlag Stuttgart · New York

Facile Approaches to 2-Deoxy-d-glucose and 2-Deoxy-α-d-glucopyranonucleosides from d-Glucal

Wenke Xu
a   School of Pharmaceutical Sciences, Zhengzhou Universit, P. R. of China   Email: fwliu@zzu.edu.cn
,
Hui Yang
a   School of Pharmaceutical Sciences, Zhengzhou Universit, P. R. of China   Email: fwliu@zzu.edu.cn
,
Yingju Liu
a   School of Pharmaceutical Sciences, Zhengzhou Universit, P. R. of China   Email: fwliu@zzu.edu.cn
,
Yingchun Hua
a   School of Pharmaceutical Sciences, Zhengzhou Universit, P. R. of China   Email: fwliu@zzu.edu.cn
,
Bin He
a   School of Pharmaceutical Sciences, Zhengzhou Universit, P. R. of China   Email: fwliu@zzu.edu.cn
,
Xin Ning
a   School of Pharmaceutical Sciences, Zhengzhou Universit, P. R. of China   Email: fwliu@zzu.edu.cn
,
Zhiyan Qin
a   School of Pharmaceutical Sciences, Zhengzhou Universit, P. R. of China   Email: fwliu@zzu.edu.cn
,
Hong-Min Liu
a   School of Pharmaceutical Sciences, Zhengzhou Universit, P. R. of China   Email: fwliu@zzu.edu.cn
b   Collaborative Innovation Center of Henan New Drug Research and Safety Evaluation, P. R. of China
,
Feng-Wu Liu*
a   School of Pharmaceutical Sciences, Zhengzhou Universit, P. R. of China   Email: fwliu@zzu.edu.cn
b   Collaborative Innovation Center of Henan New Drug Research and Safety Evaluation, P. R. of China
› Author AffiliationsFinancial support from National Natural Science Foundation of China (21372207) is gratefully acknowledged.
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Publication History

Received: 20 April 2017

Accepted after revision: 24 April 2017

Publication Date:
07 June 2017 (online)

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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 synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589501.
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