ethyl (Z)-[3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate | 69984-00-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (Z)-[3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate
• 英文别名: ethyl-(5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-D-xylo-hepto-5E-enofuranosid)
• CAS: 69984-00-5；70005-82-2
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: LIMVIYAZOAEKPQ-RXCGUALVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-[3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate 在 氨 作用下， 以 乙醇 为溶剂， 生成 ethyl 5-amino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-1,4-heptofuranuronate
  参考文献：
  名称：

  Synthesis and bioevaluation of glycosyl ureas as α-glucosidase inhibitors and their effect on mycobacterium

  摘要：

  Glycosyl amino esters (2-13) on reaction with different isocyanates resulted in quantitative conversion to glycosyl ureas (14-32). Few of the selected ureas (15-20, 22-28, 30 and 32) on cyclative amidation with DBU/TBAB/4 Angstrom MS gave respective dihydropyrimidinones in fair to good yields (33-47). The compounds were screened for alpha-glucosidase inhibitory activity and two (19 and 23) of them showed strong inhibition against rat intestinal (x-glucosidase. The compounds were also screened against Mycobacterium aurum, however, only one (19) of them exhibited marginal antitubercular activity. (C) 2000 Elsevier Science Ltd. All rights reserved. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00214-1
• 作为产物：
  描述：

  1,2-O-异亚丙基-3-O-甲基-Alpha-D-木五二呋喃醛糖-(1,4) 、 乙氧甲酰基亚甲基三苯基膦 以 苯 为溶剂， 反应 12.0h， 生成 ethyl (Z)-[3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate 、 (E)-ethyl-(3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene)-α-D-1,4-heptofuranosyl-5-enoate
  参考文献：
  名称：

  Synthesis of glycosylated β-amino acids as new class of antitubercular agents

  摘要：

  A series of glycosylated P-amino acids was prepared and evaluated against Mycohacterium tuberculosis, M. avium, M. fortuitum and M. smegmatis. The compounds were designed to mimic the enzyme D-alanine racemase and glycosyl transferase involved in the biosynthesis of essential cell wall peptidoglycan and arabinogalactan. Though most of the compounds exhibited little activity, however, one showed significant activity against all the strains in cell culture and activity was confirmed by BACTEC method. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01398-3

文献信息

• Unequivocal Experimental Evidence for a Unified Lithium Salt-Free Wittig Reaction Mechanism for All Phosphonium Ylide Types: Reactions with β-Heteroatom-Substituted Aldehydes Are Consistently Selective for<i>cis</i>-Oxaphosphetane-Derived Products
  作者：Peter A. Byrne、Declan G. Gilheany

  DOI：10.1021/ja300943z

  日期：2012.6.6

  erythro-β-hydroxyphosphonium salt) in reactions involving aldehydes bearing heteroatom substituents in the β-position. The effect operates with both benzaldehydes and aliphatic aldehydes and is shown not to operate in the absence of the heteroatom substituent on the aldehyde. The discovery of an effect that is common to reactions of all ylide types strongly argues for the operation of a common mechanism in all Li

  无锂盐维蒂希反应的真实过程长期以来一直是有机化学中一个有争议的问题。在此，我们报告了所有三种主要鏻叶立德类（非稳定化、半稳定化和稳定化）的 Wittig 反应所共有的实验效果：对顺式氧杂膦烷及其衍生产物（Z -烯烃和赤型-β-羟基鏻盐）在涉及在 β 位带有杂原子取代基的醛的反应中。该效应对苯甲醛和脂肪族醛都起作用，并且显示在醛上没有杂原子取代基的情况下不起作用。所有叶立德类型反应共有效应的发现有力地证明了所有 Li 无盐 Wittig 反应的共同机制。此外，结果表明，由 Vedejs 和同事提出的 [2+2] 环加成机制最容易解释，并由 Aggarwal、Harvey 和同事补充，从而为支持该机制提供了强有力的确证证据。值得注意的是，在半稳定叶立德的情况下，邻位取代基的协同作用得到证实，并被环加成机制所适应。该效应也显示在三苯基膦衍生的叶立德的反应中起作用，并且先前已在水性条件下的反应中观