Synthesis of oligo(spiroketal)s by polycondensation of silyl ethers derived from naturally occurring        <i >myomyo        ‐inositol with 1,4‐cyclohexanedione

Sudo Atsushi; Yamasaki Tomoki; Yamashita Takuro; Ishida Dai

摘要

ABSTRACT > Oligo(spiroketal)s (OSKs) were synthesized from myo ‐inositol, a naturally occurring cyclic compound bearing six hydroxyl groups. The successful synthesis of OSKs was achieved using silyl ethers 2 derived from 1,4‐di‐ O ‐alkylated myo ‐inositol 1 as monomers, which underwent polycondensation with 1,4‐cyclohexanedione (CHD) at 0?°C in the presence of trimethylsilyl triflate as a catalyst. Because of the irreversible nature of the condensation reaction of silyl ethers with ketones, the resulting OSKs 7 had higher molecular weights than previously reported OSKs that were obtained by polycondensation of tetraols 1 with CHD, where backward hydrolysis of the ketal functions occurred. In addition, another series of OSKs, 8, were synthesized using silyl ethers 3 derived from 2,5‐di‐ O ‐alkylated myo ‐inositol 6 , which are more symmetric monomers than silyl ethers 2 . Silyl ethers 3 underwent efficient polycondensation with CHD, whereas tetraol 6 did not, demonstrating that the derivation of such tetraols into the corresponding silyl ethers is a powerful strategy to access OSKs. ? 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019 , 57 , 2407–2414 </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><abstract type =“main”xml：lang =“en”> <标题类型=“main”>抽象</ title> > Oligo（Spiroketal）S（OSKS）合成了 myo </ i> -INOTOLOL，含有六个羟基的天然存在的环状化合物。使用甲硅烷基醚成功地合成OSK 2 </ b> 来自1,4-di- o </ i> - 烷基化 myo </ i> - 肌醇 1 </ b> 作为单体，在三甲基甲硅烷基作为催化剂的情况下在0℃下在0℃下进行1,4-环己二酮（CHD）的缩聚。由于甲硅烷基醚与酮的缩合反应的不可逆转性质，所得到的OSK 7 </ b> 分子量高于先前报告的osk，其通过缩聚的四元溶解而获得 1 </ b> 用CHD，发生缩缩功能的后水解水解。另外，另一系列osk， 8，</ b> 使用Silyl ethers合成 3 </ b> 衍生自2,5-二 - o </ i> - 烷基化 myo </ i> - 肌醇 6 </ b> ，这比甲硅烷基醚更对称单体 2 </ b> 。甲岛醚 3 </ b> 随着CHD的高效缩聚，而Tetraol 6 </ b> 展示这种四元醇进入相应的甲硅烷基醚的推导是访问OSK的强大策略。还是2019 Wiley期刊，Inc.J.Colom。 SCI。，A部分：polym。化学。 2019 </ b> 那 57 </ i> ，2407-2414 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-35621/'>《Journal of Polymer Science, Part A. Polymer Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2019年第24期</span><b style="margin: 0 2px;">|</b><span>共8页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sudo Atsushi&option=202" target="_blank" rel="nofollow">Sudo Atsushi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yamasaki Tomoki&option=202" target="_blank" rel="nofollow">Yamasaki Tomoki;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yamashita Takuro&option=202" target="_blank" rel="nofollow">Yamashita Takuro;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ishida Dai&option=202" target="_blank" rel="nofollow">Ishida Dai;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Graduate School of Science and Engineering ResearchKindai University Kowakae 3‐4‐1 Higashi OsakaOsaka 577‐8502 Japan;</p> <p>Graduate School of Science and Engineering ResearchKindai University Kowakae 3‐4‐1 Higashi OsakaOsaka 577‐8502 Japan;</p> <p>Graduate School of Science and Engineering ResearchKindai University Kowakae 3‐4‐1 Higashi OsakaOsaka 577‐8502 Japan;</p> <p>Graduate School of Science and Engineering ResearchKindai University Kowakae 3‐4‐1 Higashi OsakaOsaka 577‐8502 Japan;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1184.html" title="有机化学">有机化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=high performance polymers&option=203" rel="nofollow">high performance polymers;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=myo ‐inositol&option=203" rel="nofollow">myo ‐inositol;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=oligo(spiroketal)&option=203" rel="nofollow">oligo(spiroketal);</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=renewable resources&option=203" rel="nofollow">renewable resources;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=silyl ether&option=203" rel="nofollow">silyl ether;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=step‐growth polymerization&option=203" rel="nofollow">step‐growth polymerization;</a> </p> <div class="translation"> 机译：高性能聚合物;Myo-inositol;oligo（螺旋液）;可再生资源;甲硅烷基醚;步进 - 生长聚合; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704020725730.html">Synthesis of oligo(spiroketal)s by polycondensation of silyl ethers derived from naturally occurring <i >myomyo ‐inositol with 1,4‐cyclohexanedione</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sudo Atsushi&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Sudo Atsushi,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yamasaki Tomoki&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Yamasaki Tomoki,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yamashita Takuro&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Yamashita Takuro,</a> <a href="/journal-foreign-35621/" target="_blank" rel="nofollow" class="tuijian_authcolor">Journal of Polymer Science, Part A. 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<a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=余金权&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,余金权</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=陈欣权&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,陈欣权</a> <span> <a href="/journal-cn-15847/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 有机化学 </a> </span> <span> . 1992</span><span>,第2期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-37627_thesis/020221606847.html">界面缩聚法合成双（烷基环戊二烯基）钛（锆）聚醚、酯、醚酯、胺、胺酯的研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=沈宏康&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 沈宏康</a> <span> <a href="/conference-cn-37627/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 华北四省市首届化学年会 </a> <span> <span> . 1987</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020312219072.html">N-（三丁基锡甲氧基烷基醚）邻苯二甲酰亚胺光诱导成环反应</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张鹏&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 张鹏</a> <span> . 2012</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120104396875.html">N－ω－(甲基),ω－(甲硅烷基)烷基－N－有机羧酰胺、其低聚和缩聚含硅化合物、其制备方法和用途</a> <b>[P]</b> . <span> 中国专利： CN1202491A </span> <span> . 1998-12-23</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120106261941.html">新颖的甲硅烷基取代的1,4-二硅环己烷衍生物及其制备方法</a> <b>[P]</b> . <span> 中国专利： CN102066387A </span> <span> . 2011-05-18</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130420371369.html">MICROBIAN BIOCATALIZERS NOT NATURALLY OCCURING AND METHODS FOR 4-HYDROXIBUTANOIC ACID BIOSYNTHESIS AND 1,4-BUTANHYDROL</a> <b>[P]</b> . <span> 外国专利：  BRPI0823327A2 </span> <span> . 2013-10-22</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：非自然发生的微生物生物催化剂和4-羟基布丁酸生物合成和1,4-丁二醇的方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130403558673.html">METHOD FOR ASSESSING SUITABILITY OF ARTIFICIAL PROTEIN INCLUDING AMINO ACID RESIDUE DERIVED FROM NON-NATURALLY-OCCURRING AMINO ACID, FOR SYNTHESIS BY RIBOSOMES</a> <b>[P]</b> . <span> 外国专利：  WO2019049663A1 </span> <span> . 2019-03-14</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：核糖体合成的非天然氨基酸衍生物的人工蛋白质适宜性评估方法，包括氨基酸残基 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130462847753.html">Prepn. of methyl:alkoxy:oligo(di:silyl)-siloxane cpds. - by two stage alkoxylation of distn. residue from methyl:chlorosilane synthesis or di:silane(s) from residue</a> <b>[P]</b> . <span> 外国专利：  DE4033156A1 </span> <span> . 1992-04-16</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：准备甲基：烷氧基：低聚（二：甲硅烷基）-硅氧烷cpds。 -由distn的两阶段烷氧基化。来自甲基：氯硅烷合成的残留物或来自残留物的二：硅烷 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" 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Synthesis of oligo(spiroketal)s by polycondensation of silyl ethers derived from naturally occurring myomyo ‐inositol with 1,4‐cyclohexanedione

摘要