methyl 2,3:4,6-di-O-isopropylidene-α-L-xylo-2-hexulofuranosonate | 52507-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3:4,6-di-O-isopropylidene-α-L-xylo-2-hexulofuranosonate
• 英文别名: 2,3;4,6-Di-O-isopropyliden-L-gulonsaeuremethylester；2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid methyl ester；methyl 2,3:4,6-di-O-isoprpylidene-α-L-xylo-hex-2-ulofuranosonate；O²,O³;O⁴,O⁶-diisopropylidene-α-L-xylo-[2]hexulofuranosonic acid methyl ester；O²,O³;O⁴,O⁶-Diisopropyliden-α-L-xylo-[2]hexulofuranosonsaeure-methylester；2,3:4,6-di-O-isopropylidene-xylo-2-hexulofuranosonic acid methyl ester；Zegnzpmitnpdhg-qridjokksa-；methyl (1R,2S,6R,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane-6-carboxylate
• CAS: 52507-90-1
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: ZEGNZPMITNPDHG-QRIDJOKKSA-N

物化性质

• 沸点：
  358.8±42.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3:4,6-di-O-isopropylidene-α-L-xylo-2-hexulofuranosonate 在 copper diacetate 作用下， 以 水 为溶剂， 反应 0.08h， 以13 g的产率得到methyl 2,3-O-isopropylidene-L-lyxo-hex-2-ulofuranosate
  参考文献：
  名称：

  6-脱氧-6-卤素-L-Ascorbinsäure的合成和本征交换†

  摘要：

  L-抗坏血酸的6-脱氧-6-卤代衍生物的合成及性质

  DOI：

  10.1002/hlca.19800630642
• 作为产物：
  描述：

  调呋酸 在 重氮甲烷 、 甲醇 作用下， 生成 methyl 2,3:4,6-di-O-isopropylidene-α-L-xylo-2-hexulofuranosonate
  参考文献：
  名称：

  Sumiki; Mitsunaga, Nippon Nogeikagaku Kaishi, 1951, vol. 25, p. 198

  摘要：

  DOI：

文献信息

• A strategy for generating alkyl radicals from aliphatic esters and lactones via sequential hydrolysis and photoinduced decarboxylation
  作者：Hikaru Saito、Takayuki Kanetake、Kazuyuki Osaka、Kousuke Maeda、Toshio Morita、Yasuharu Yoshimi

  DOI：10.1016/j.tetlet.2015.02.020

  日期：2015.3

  photoinduced decarboxylation of methyl aliphatic esters lead to efficient generation of alkyl radicals under mild conditions. The generated alkyl radicals react with a variety of reagents to produce addition, reduction, and substitution products. In addition, the new tin and halogen free process for alkyl radical generation is applicable to a variety of aliphatic esters including those of dipeptides, steroids

  甲基脂族酯的顺序水解和光诱导的脱羧作用导致在温和条件下有效生成烷基。生成的烷基与多种试剂反应，生成加成，还原和取代产物。另外，用于产生烷基自由基的新的无锡和卤素的方法适用于多种脂族酯，包括二肽，类固醇，糖和内酯。
• Nucleophilic Catalysis with 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) for the Esterification of Carboxylic Acids with Dimethyl Carbonate
  作者：Wen-Chung Shieh、Steven Dell、Oljan Repič

  DOI：10.1021/jo011036s

  日期：2002.4.1

  0]undec-7-ene (DBU) is an effective nucleophilic catalyst for carboxylic acid esterification with dimethyl carbonate (DMC). The reaction pathway of this new class of nucleophilic catalysis has been studied. A plausible, multistep mechanism is proposed, which involves an initial N-acylation of DBU with DMC to form a carbamate intermediate. Subsequent O-alkylation of the carboxylate with this intermediate

  1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）是一种有效的亲核催化剂，用于碳酸二甲酯（DMC）进行羧酸酯化。已经研究了这种新型亲核催化的反应途径。提出了一种可行的多步机制，该机制涉及DBU与DMC的初始N酰化反应以形成氨基甲酸酯中间体。随后用该中间体使羧酸酯的O-烷基化以优异的产率产生相应的甲酯。在没有DBU的情况下或在其他碱例如氢氧化铵或N-甲基吗啉的存在下，相同的反应没有得到所需的产物。该方法对于合成含有酸敏感性官能团的甲酯特别有价值。
• A new version of the reverse-Cope elimination initiated by the nucleophilic addition of allylamines to nitrones: a synthesis of vicinal diamines
  作者：Michael B. Gravestock、David W. Knight、K. M. Abdul Malik、Steven R. Thornton

  DOI：10.1039/b003959o

  日期：——

  are successful, giving the trans-oxadiazinanes 24, 33 and the stereoisomers 38 and 39 from linalylamine 37, but only when the terminus of the allylamine is unsubstituted are the reactions efficient. A range of N-alkylallylamines 43, 45, 47 and 49, however, react smoothly with nitrone 8, as competing imine formation is precluded. Various mechanistic aspects are discussed, along with the effects of aryl

  尝试在与被保护的烯丙胺6进行对映选择性[1,3]偶极环加成反应中使用糖衍生的硝酮1只是部分成功，得到了预期加合物的混合物7。但是，硝酮1和未保护的烯丙胺11之间的反应遵循不同的途径，涉及通过胺，反向应对 环化和Meisenheimer重排导致1,2,5- oxadiazinanes 12和13。与类似的反应苯甲醛衍生的硝酮8是成功的，赋予反-oxadiazinanes 24，33和立体异构体38和39从芳基胺 如图37所示，但是只有当烯丙基胺的末端未被取代时，反应才有效。的范围Ñ -alkylallylamines 43，45，47和49，但是，与硝酮顺利反应8，如竞争性亚胺排除形成。讨论了各种机械方面，以及以下方面的影响：芳基在N-苄基烯丙胺57中和在硝酮8的4-位（59）处的取代基，没有发现可以提高总反应速率的取代基。最初的恶二嗪酮可用作氨基羟胺69和邻位的前体二胺衍生物70。
• Microwave irradiation process for preparing methyl esters
  申请人：——

  公开号：US20030144543A1

  公开（公告）日：2003-07-31

  An accelerated process for preparing a methyl ester having formula (III) 1 said process comprising reacting a carboxylic acid or salt thereof having formula (I) 2 with dimethyl carbonate having formula (II) 3 in the presence of a catalyst selected from the group consisting of 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; 4-dimethylaminopyridine; and combinations thereof, wherein R 1 is selected from the group consisting of an alkyl, aryl, alkoxy, alkenyl, cycloalkyl, benzocycloalkyl, cycloalkylalkyl, aralkyl, heterocyclic, heteroaralkyl, alkoxyalkyl, carboxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, and haloalkyl; and M is selected from the group consisting of hydrogen, a monovalent metal, and a monovalent fractional part of a polyvalent metal, wherein said process is conducted under microwave irradiation at a frequency from 300 MHz to 30 GHz, and at a temperature of from about 120° C. to 300° C. for a period of microwave irradiation time from about 1 second to about 300 minutes. The process of the invention is especially advantageous for preparing methyl esters since the process: (1) utilizes an environmentally friendly methylating reagent, dimethylcarbonate; (2) produces a high yield of the methyl ester, generally 95-99% conversion in less than 30 minutes of microwave irradiation; (3) minimizes degradation and/or racemization of optically pure compounds; and (4) minimizes the formation of by-products.

  一种加速制备具有式（III）甲酯的过程，包括在催化剂的存在下，将具有式（I）的羧酸或其盐与具有式（II）的碳酸二甲酯反应，所述催化剂选择自1,8-二氮杂双环[5.4.0]-十一烯；1,4-二氮杂双环[2.2.2]-辛烷；4-二甲基氨基吡啶和其组合物，其中R1选自烷基，芳基，烷氧基，烯基，环烷基，苯并环烷基，环烷基烷基，芳基烷基，杂环基，杂芳基烷基，烷氧基烷基，羧基烷基，烷基羰基，烷氧羰基烷基和卤代烷基；M选自氢，一价金属和多价金属的一价分数部分，其中所述过程在微波辐射下进行，频率从300 MHz到30 GHz，温度从约120℃到300℃，微波辐射时间为约1秒到约300分钟。本发明的过程特别适用于制备甲酯，因为该过程：（1）利用环保的甲基化试剂，碳酸二甲酯；（2）产量高，通常在30分钟内微波辐射下转化率达95-99％；（3）最小化光学纯化合物的降解和/或外消旋化；（4）最小化副产物的形成。
• CONJUGATES OF ANTIOXIDANTS WITH METAL CHELATING LIGANDS FOR USE IN DIAGNOSTIC AND THERAPEUTIC APPLICATIONS
  申请人：Ranganathan S. Ramachandran

  公开号：US20070086944A1

  公开（公告）日：2007-04-19

  The invention provides radiopharmaceuticals for diagnostic and therapeutic applications, conjugates of antioxidants with metal chelating ligands, intermediate compounds, methods of making such radiopharmaceuticals, ligands, and intermediate compounds, and kits for preparing the radiopharmaceutical complexes.

  该发明提供了用于诊断和治疗应用的放射性药物、抗氧化剂与金属螯合配体的结合物、中间化合物、制备这种放射性药物、配体和中间化合物的方法，以及用于制备放射性药物复合物的试剂盒。