open access

https://hdl.handle.net/2115/82288

Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum Salts

英語

N-acetylglucosamine dehydration

2020-07-22

Wiley-Blackwell

ChemSusChem

13(14)

3594-3598

3-Acetamido-5-acetylfuran (3A5AF) is a promising intermediate obtained from chitin for the production of N-containing value-added chemicals. However, the synthetic method is complicated so far, which has limited further investigation using 3A5AF. Herein, a facile method was developed for synthesizing 3A5AF from N-acetyl-d-glucosamine (NAG), including a simple isolation procedure. A 30 % yield of 3A5AF was obtained by performing the dehydration of NAG in N,N-dimethylformamide (DMF) solvent in the presence of AlCl3.6 H2O at a temperature as low as 120 degrees C by conventional heating for 30 min. This method tolerated a wide range of temperature and concentration of substrate, thus easily allowing scale-up of the reaction. The produced 3A5AF was isolated with 98 % purity by simple column chromatography. Additionally, a highly functionalized N-containing lactone was identified as a byproduct under these reaction conditions.

学術雑誌論文

Accepted Manuscript

This is the peer reviewed version of the following article: D. Padovan, H. Kobayashi, A. Fukuoka, Facile Preparation of 3‐Acetamido‐5‐acetylfuran from N‐Acetyl‐d‐glucosamine by using Commercially Available Aluminum Salts, ChemSusChem 2020, 13, 3594, which has been published in final form at https://doi.org/10.1002/cssc.202001068 . This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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