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Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase.

ABSTRACT: A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly used protecting bulky groups for primary hydroxyl groups, the benzoyl protective group offers a new protection strategy.

SUBMITTER: Lu Y

PROVIDER: S-EPMC6274181 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase.

Lu Yuchao Y Hou Chenxi C Ren Jingli J Xin Xiaoting X Xu Hengfu H Pei Yuxin Y Dong Hai H Pei Zhichao Z

Molecules (Basel, Switzerland) 20160517 5

A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly used protecting bulky groups for primary hydroxyl groups, the benzoyl protective group offers ...[more]

PMID: 27196888

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