CAS: 37112-31-5; (1S,5R)-6,8-Dioxabicyclo[3.2.1]Oct-2-En-4-One

该化合物是一种双环氢素,产自纤维素或碳水化合物富集生物量的热解.它是有机合成的多用途手动建筑块,提供硬性,含氧量强的手脚架,配有反应功能组,包括一个氯酮和单体.它的独特结构使得药物,农用化学品和细化化学品的应用成为可能,特别是作为立体选择性转化的前体.Levoglucosenone因其可再生来源而备受重视,为石油衍生中间体提供了可持续的替代物.它在受控条件下的高度纯度和稳定性使其适合高要求的合成工艺.该复合体的再活性和性也促进了对等纯化合物的生产,提高了其在非对称合成合成中的效用.

结构式图片

相似化合物

115509-13-2 281676-64-0 1212181-78-6

欧盟法规

C&L通报

上下游产品

1,6-Anhydro-3,4-Dideoxy-β-D-Threo-Hex-3-Enopyranose 50705-28-7
1,6-Anhydro-3,4-Dideoxy-β-D-Erythro-Hex-3-Enopyranose 58394-28-8

合成工艺路线路线简述

  • 合成目标产物 Levoglucosenone 主要起始原料 .Beta.-D-Erythro-Hexopyranos-2-Ulose, 1,6-Anhydro-3-Deoxy-
  • (文献来源)合成步骤主要原料 .Beta.-D-Erythro-Hexopyranos-2-Ulose, 1,6-Anhydro-3-Deoxy-
📜1,6-脱水-β-D-葡萄糖置于1-丙磺酸体系中,用 四氢呋喃 用作溶剂,209.84 °C,6.9 Mpa 条件下,反应生成左旋葡萄糖酮
参考文献:Catalytic Dehydration Of Levoglucosan To Levoglucosenone Using Brønsted Solid Acid Catalysts In Tetrahydrofuran
标题:Catalytic Dehydration Of Levoglucosan To Levoglucosenone Using Brønsted Solid Acid Catalysts In Tetrahydrofuran
摘要:我们使用丙基磺酸功能化的硅胶从乙基葡萄糖苷中生产了59%选择性,转化率为100%.
Doi:10.1039/c9Gc01526D

海关参考信息

专利信息


专利号:US-2024368099-A1
优先权日:2022-01-18
标 题:Methods for the synthesis of di(hydroxymethyl)tetrahydrofuran and its application in polyesters and polyurethanes
发明人:SPIEGELBERG BRIAN; BRANDT ADRIAN; BECK HORST; KUX ALEXANDER; TIN SERGEY; DE VRIES JOHANNES GERARDUS
权利人:HENKEL AG & CO KGAA
摘要:The present invention relates to the synthesis of di(hydroxymethyl)tetrahydrofuran (DHMTHF) and the preparation of trans-enriched mixtures of DHMTHF. The invention further refers to polyester polyols which are obtained by reaction of cis/trans DHMTHF mixtures with a dicarboxylic acid. The invention further relates to polyurethanes and compositions containing a polyester polyol comprising DHMTHF, in particular to such polyurethane-containing (adhesive) compositions.

专利号:US-9873612-B2
优先权日:2013-10-29
标 题:Catalytic formation of carbon monoxide (CO) and hydrogen (H2) from biomass
发明人:NEUMANN RONNY; SARMA Bidyut-Bikash
权利人:YEDA RES & DEV; YEDA RES & DEV
摘要:The present invention relates to methods of preparing carbon monoxide (CO) and hydrogen (H 2 ) by reacting biomass, a biomass component (e.g., lignin, ligno-cellulose, cellulose, hemiceullose or combination thereof) or a carbohydrate from any source with a polyoxometalate catalyst such as H 5 PV 2 Mo 10 O 40 , or solvates thereof, in the presence of a concentrated acid, under conditions sufficient to yield carbon monoxide (CO); followed by electrochemical release of hydrogen (H 2 ). The carbon monoxide (CO) and hydrogen (H 2 ) may be combined in any desired proportion to yield synthesis gas (Syngas). The present invention further relates to methods for preparing H 2 , CO and formic acid/formaldehyde from biomass, a biomass component and/or from carbohydrates.

专利号:US-10364265-B1
优先权日:2015-12-15
标题:Anhydrosugar synthesis
发明人:CHEN LI; WONG MICHAEL S; ZHANG ZONGCHAO
权利人:WILLIAM MARSH RICE UNIVERISTY; UNIV RICE WILLIAM M
摘要:Improved methods of making anhydrosugars by pyrolysis of a substrate sugar to remove at least one water molecule thereby producing a desired anhydrosugar and side products, the improvement being either 1) protecting one hydroxyl group of the substrate sugar before pyrolysis; or (2) pretreating the substrate sugar with a metal salt and optional acid before pyrolysis, wherein lower amounts of said side products are produced by said improved method.

专利号:US-5457192-A
优先权日:1991-02-21
标题 :Method of manufacturing D-allosan
发明人:MATSUMOTO KATSUYA; EBATA TAKASHI; MATSUSHITA HAJIME
权利人:JAPAN TOBACCO INC
摘要:PCT No. PCT/JP92/00170 Sec. 371 Date Oct. 21, 1992 Sec. 102(e) Date Oct. 21, 1992 PCT Filed Feb. 19, 1992 PCT Pub. No. WO92/14744 PCT Pub. Date Sep. 3, 1992.The carbonyl group at the 2-position of levoglucosenone is reduced to obtain a hydroxyl group having a beta -configuration. The hydroxyl group having a beta -configuration is reversed to an alpha -configuration, and hydroxyl groups are added at the 3- and 4-positions in a cis- alpha form. Finally, the protective group of the hydroxyl group at the 2-position is eliminated. The reduction of the carbonyl group at the 2-position can be performed such that the levoglucosenone is reacted with aluminum lithium hydride or sodium boron hydride in an appropriate solvent. Reversion of the hydroxyl group having a beta -configuration can be performed by the Mitsunobu method or a method having a mesylation step and a step using cesium acetate. The addition of the hydroxyl groups to the 3-and 4-positions in the cis form can be performed by oxidizing the double bond across the 3- and 4-positions with an appropriate oxidizing agent. The elimination of the protective group of the hydroxyl group at the 2-position can be performed under basic conditions in accordance with normal methods. According to the method of the present invention, D-allosan can be obtained stereoselectively in high yield via a smaller number of steps than that of the conventional synthesis method.

专利号:BR-102020021669-A2
优先权日:2020-10-22
标 题:Process of synthesis of long-chain polyols from biomass and compounds obtained

专利号:JP-2025504449-A
优先权日:2022-01-18
标题 :Synthesis of di(hydroxymethyl)tetrahydrofuran and its application in polyesters and polyurethanes.

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献


1: Sarnik J, Czubatka-Bienkowska A, Macieja A, Bielski R, Witczak ZJ, Poplawski T. The induction of oxidative stress in cervix carcinoma cells by levoglucosenone derived 4-S-salicyl derivative and (1-4)-S-thio-disaccharides. Part 4. Bioorg Med Chem Lett. 2017 Mar 1;27(5):1215-1219. doi: 10.1016/j.bmcl.2017.01.064. Epub 2017 Jan 22. doi: 10.1002/cssc.201601308. Epub 2016 Dec 13. doi: 10.1002/cssc.201600795. Epub 2016 Nov 17. pii: E988. doi: 10.3390/molecules21080988. doi: 10.1039/c6ob00933f. Epub 2016 Jul 18. doi: 10.1016/j.bmcl.2016.07.007. Epub 2016 Jul 4. doi: 10.3389/fchem.2016.00016. eCollection 2016.
8: Comba MB, Suárez AG, Sarotti AM, Mangione MI, Spanevello RA, Giordano ED. Synthesis of a 3-Thiomannoside. Org Lett. 2016 Apr 15;18(8):1748-51. doi: 10.1021/acs.orglett.6b00428. Epub 2016 Apr 7. doi: 10.1016/j.pharmthera.2016.03.010. Epub 2016 Mar 22. Review. doi: 10.1021/acs.joc.5b01214. Epub 2015 Jul 24. doi: 10.1016/j.biortech.2014.11.105. Epub 2014 Dec 4. doi: 10.1016/j.carres.2014.07.019. Epub 2014 Aug 1. doi: 10.1016/j.biortech.2014.08.075. Epub 2014 Aug 23. doi: 10.1016/j.carres.2014.03.017. Epub 2014 Mar 22. doi: 10.1021/jo500527g. Epub 2014 Apr 15. doi: 10.1021/ol302061a. Epub 2012 Aug 24. doi: 10.1021/ol3008588. Epub 2012 Apr 30. doi: 10.1016/j.biortech.2011.10.078. Epub 2011 Oct 30. doi: 10.1016/j.biortech.2011.10.010. Epub 2011 Oct 12. doi: 10.1002/cssc.201000210. Epub 2010 Nov 12.

合成参考文献


参考文献:10.1055/s-2006-926325
摘要:Ishikawa T, Kumamoto T. Guanidines in Organic Synthesis. Synthesis. 2006;2006(05):737–52. doi: 10.1055/s-2006-926325.
参考文献:10.1007/s10924-023-03118-z
摘要:Freije García F, García Liñares G. Use of Lipases as a Sustainable and Efficient Method for the Synthesis and Degradation of Polymers. J Polym Environ. 2023 Nov 27;32(5):2484–516. doi: 10.1007/s10924-023-03118-z.
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