TY - JOUR
T1 - Formation of five-membered carbocycles from D-glucose
T2 - A Concise Synthesis of 4-Hydroxy-2-(hydroxymethyl)cyclopentenone
AU - Koseki, Yoshitaka
AU - Watanabe, Toshihiro
AU - Kamishima, Takaaki
AU - Kwon, Eunsang
AU - Kasai, Hitoshi
N1 - Funding Information:
We would like to thank Prof. Shigefumi Kuwahara and Dr. Masaru Enomoto of Tohoku University for their help with measurements of the specific optical rotation. We also thank Prof. Masaya Mitsuishi and Mr. Hiroaki Ohara for their help with FT-IR measurements. In addition, we would like to thank Dr. Toshiyuki Nonaka of FromSeeds Co., Dr. Shigenobu Aoyagi of Ouchi Shinko Chemical Industrial Co., Ltd., and Prof. Masaru Watanabe of Tohoku University for productive discussions. This study was financially supported by the Shorai Fundation for Science and Technology, the Cooperative Research Program “Network Joint Research Center for Materials and Devices” and the Research Program “Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials”.
Publisher Copyright:
© 2019 The Chemical Society of Japan.
PY - 2019
Y1 - 2019
N2 - A concise synthesis of 4-hydroxy-2-(hydroxymethyl)cyclo-pentenone (1) has been accomplished from D-glucose by a three-step sequence that features a catalyst-free hydrothermal reaction of D-glucal, which is readily obtained from D-glucose. Optimization of the reaction conditions for synthesizing 1 was performed by changing the temperature and reaction time. The treatment of D-glucal under the optimal conditions, i.e., at 120 °C for 24 h, provided 1 in the highest isolated yield of 61%. 1 would become a versatile intermediate for the synthesis of various fine chemicals having a cyclopentenone structure from cellulosic biomass.
AB - A concise synthesis of 4-hydroxy-2-(hydroxymethyl)cyclo-pentenone (1) has been accomplished from D-glucose by a three-step sequence that features a catalyst-free hydrothermal reaction of D-glucal, which is readily obtained from D-glucose. Optimization of the reaction conditions for synthesizing 1 was performed by changing the temperature and reaction time. The treatment of D-glucal under the optimal conditions, i.e., at 120 °C for 24 h, provided 1 in the highest isolated yield of 61%. 1 would become a versatile intermediate for the synthesis of various fine chemicals having a cyclopentenone structure from cellulosic biomass.
KW - Biomass feedstock
KW - Glucose conversion
KW - Hydrothermal reaction
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U2 - 10.1246/bcsj.20190063
DO - 10.1246/bcsj.20190063
M3 - Article
AN - SCOPUS:85072201269
SN - 0009-2673
VL - 92
SP - 1324
EP - 1328
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 8
ER -