Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates

doi:10.1007/s40242-013-2293-6

高等学校化学研究 ›› 2013, Vol. 29 ›› Issue (3): 551-555.doi: 10.1007/s40242-013-2293-6

Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates

PAN Xiao-liang¹, ZHOU Yi-xuan², LIU Wei¹, LIU Jing-yao¹, DONG Hai²

1. State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun 130021, P. R. China;
2. School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, P. R. China

收稿日期:2012-08-06 修回日期:2012-09-26 出版日期:2013-06-01 发布日期:2013-05-15
通讯作者: LIU Jing-yao, E-mail: ljy121@jlu.edu.cn; DONG Hai, E-mail: hdong@mail.hust.edu.cn E-mail:ljy121@jlu.edu.cn; hdong@mail.hust.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.20973077), the Program for New Century Excellent Talents in University of China(No.NCET-07-0358) and the Brain Gain Fund of Huazhong University of Science and Technology, China.

Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates

PAN Xiao-liang¹, ZHOU Yi-xuan², LIU Wei¹, LIU Jing-yao¹, DONG Hai²

1. State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun 130021, P. R. China;
2. School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, P. R. China

Received:2012-08-06 Revised:2012-09-26 Online:2013-06-01 Published:2013-05-15
Contact: Jing-yao Liu E-mail:ljy121@jlu.edu.cn; hdong@mail.hust.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.20973077), the Program for New Century Excellent Talents in University of China(No.NCET-07-0358) and the Brain Gain Fund of Huazhong University of Science and Technology, China.

摘要/Abstract

摘要：

A mechanism about the origin of the selectivities for the cleavage of dioxolane five-membered rings on pyranoside rings was suggested. Quantum chemical studies were performed to testify the rationality of the mechanism. It is thus suggested that the selectivities should be dependent on the differences of the free energy at the transition states when the five-membered ring cleaves. Natural bond orbital(NBO) analysis was further made to assess the influence of stereoelectronic effects on the selectivities.

关键词: Stereoelectronic effect, Carbohydrate, Antiperiplanar lone-pair hypothesis

Abstract:

Key words: Stereoelectronic effect, Carbohydrate, Antiperiplanar lone-pair hypothesis

PAN Xiao-liang, ZHOU Yi-xuan, LIU Wei, LIU Jing-yao, DONG Hai. Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates[J]. 高等学校化学研究, 2013, 29(3): 551-555.

PAN Xiao-liang, ZHOU Yi-xuan, LIU Wei, LIU Jing-yao, DONG Hai. Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates[J]. Chemical Research in Chinese Universities, 2013, 29(3): 551-555.

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Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates

Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates

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