Formation of Five-Membered Carbocycles from D-Glucose: A Concise Synthesis of 4-Hydroxy-2-(hydroxymethyl)cyclopentenone

Koseki Yoshitaka; Watanabe Toshihiro; Kamishima Takaaki; Kwon Eunsang; Kasai Hitoshi

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Formation of Five-Membered Carbocycles from D-Glucose: A Concise Synthesis of 4-Hydroxy-2-(hydroxymethyl)cyclopentenone

机译：从D-葡萄糖形成五元碳键：4-羟基-2-（羟甲基）环戊烯酮的简洁合成

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A concise synthesis of 4-hydroxy-2-(hydroxymethyl)cyclopentenone (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 degrees 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.

机译：通过三步序列通过D-葡萄糖的D-葡萄糖完成了4-羟基-2-（羟甲基）环戊烯酮（1）的简明合成，其具有D-葡萄糖的催化剂的水热反应，其易于从D-中获得葡萄糖。通过改变温度和反应时间来进行合成1的反应条件的优化。在最佳条件下，在120℃下，在24小时的最高分离产率为61％的情况下处理D-葡萄糖。 1将成为合成具有来自纤维素生物质的环戊烯结构的各种精细化学品的多功能中间体。

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《Bulletin of the Chemical Society of Japan》 |2019年第8期|共5页
作者
Koseki Yoshitaka; Watanabe Toshihiro; Kamishima Takaaki; Kwon Eunsang; Kasai Hitoshi;
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作者单位

Tohoku Univ Inst Multidisciplinary Res Adv Mat Aoba Ku 2-1-1 Katahira Sendai Miyagi 9808577 Japan;

Tohoku Univ Inst Multidisciplinary Res Adv Mat Aoba Ku 2-1-1 Katahira Sendai Miyagi 9808577 Japan;

Tohoku Univ Inst Multidisciplinary Res Adv Mat Aoba Ku 2-1-1 Katahira Sendai Miyagi 9808577 Japan;

Tohoku Univ Grad Sch Sci Res &

Analyt Ctr Giant Mol Aoba Ku 6-3 Aramaki Aza Aoba Sendai Miyagi 9808578 Japan;

Tohoku Univ Inst Multidisciplinary Res Adv Mat Aoba Ku 2-1-1 Katahira Sendai Miyagi 9808577 Japan;

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正文语种 eng
中图分类化学;
关键词
Glucose conversion; Hydrothermal reaction; Biomass feedstock;

机译：葡萄糖转化;水热反应;生物质原料;

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专利

1. Formation of Five-Membered Carbocycles from D-Glucose: A Concise Synthesis of 4-Hydroxy-2-(hydroxymethyl)cyclopentenone [J] . Koseki Yoshitaka, Watanabe Toshihiro, Kamishima Takaaki, Bulletin of the Chemical Society of Japan . 2019,第8期

机译：从D-葡萄糖形成五元碳键：4-羟基-2-（羟甲基）环戊烯酮的简洁合成
2. Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides. [J] . Choi WJ, Moon HR, Kim HO, Nucleosides, nucleotides and nucleic acids . 2005,第5a7期

机译：立体选择合成3-羟甲基-D-环戊烯酮，这是合成碳环核苷的通用中间体。
3. Photoinduced Carboborative Ring Contraction Enables Regio- and Stereoselective Synthesis of Multiply Substituted Five-Membered Carbocycles and Heterocycles [J] . Shengfei Jin, Vu T. Nguyen, Hang T. Dang, Journal of the American Chemical Society . 2017,第33期

机译：光诱导的碳环收缩使多元取代的五元碳环和杂环的区域和立体选择性合成成为可能。
4. Synthesis of Eleven-membered Carbocycle via Ando- olefination andHomo-Cope Ring Expansion [C] . Hideyuki Suzuki 11th International Symposium of Fine Chemistry and Functional Polymers Jul 28-31, 2001 Hailar, Inner Mongolia, P.R. China . 2001

机译：烯-烯烃化和均相扩环合成十一元碳环
5. Development of new syntheses and transformations of beta-lactones: Application to a concise total synthesis of (+)-brefeldin A. [D] . Wang, Yingcai. 2002

机译：β-内酯的新合成和转化的开发：在简明的（+）-布雷菲德菌素A的全合成中的应用。
6. Photoinduced Carboborative Ring Contraction Enables Regio- and Stereoselective Synthesis of Multiply Substituted Five-Membered Carbocycles and Heterocycles [O] . Shengfei Jin, Vu T. Nguyen, Hang T. Dang, -1

机译：光诱导的碳环收缩使多元取代的五元碳环和杂环的区域和立体选择性合成成为可能。
7. A New Class of Substrates for Nucleophilic 5-endo-trig Cyclization, 2-Trifluoromethyl-1-alkenes: Synthesis of Five-Membered Hetero- and Carbocycles That Bear Fluorinated One-Carbon Units [O] . Ichikawa Junji, Iwai Yu, Nadano Ryo, 2008

机译：一类新型的亲核性5-内-trig环化，2-三氟甲基-1-烯烃的基质：带有氟化一碳单元的五元杂环和碳环的合成。

Formation of Five-Membered Carbocycles from D-Glucose: A Concise Synthesis of 4-Hydroxy-2-(hydroxymethyl)cyclopentenone

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