methyl (2Z)-2-[(3aR,6R,6aR)-6-(acetyloxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ylidene]acetate | 1374429-63-6

• 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: methyl (2Z)-2-[(3aR,6R,6aR)-6-(acetyloxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ylidene]acetate
• CAS: 1374429-63-6
• 化学式: C₁₃H₁₈O₇
• 分子量: 286.282
• InChiKey: NIRJVKDBWGEXDB-RCZLXPMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2Z)-2-[(3aR,6R,6aR)-6-(acetyloxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ylidene]acetate 在 4-二甲氨基吡啶 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium 、 sodium ascorbate 、 三乙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 105.0h， 生成 (3'R,3aR,4S,4'S,6R,6aR) dihydro-6-[[(2S)-4-[N-((4-guanidino-2-hydroxycarbonyl)butyl)carboxamide]-1,2,3-triazol-1-yl]methyl]-2,2,2'-trimethyl-3'-phenylspiro[furo[3,4-d]-1,3-dioxole-4(3aH),5'-isoxazolidine]-4'-carboxylic acid
  参考文献：
  名称：

  Spiro sugar-isoxazolidine scaffold as useful polyfunctional building block for peptidomimetics design

  摘要：

  Spiro sugar-isoxazolidines obtained by 1,3-dipolar cycloaddition of activated exo-glycals and nitrones were efficiently functionalized at two sites, i.e. C-4 and C-7, with arginine, arginine mimetics and guanidylated appendages. Two bicyclic sugar derivatives differing by the configuration at C-7 were chosen as model compounds. The small library of peptidomimetics was evaluated toward inhibition of VEGF-A165/neuropilin-1 binding. Unexpected cleavage of C3-C4 bond of isoxazolidine moiety was observed during hydrogenolysis and opened thus a new way toward hemiketal structures which could also find interesting applications as less constrained scaffold. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2016.01.005

文献信息

• Base- and Radical-Mediated Regio- and Stereoselective Additions of Thiols, Thio-Sugars, and Thiol-Containing Peptides to Trisubstituted Activated<i>exo</i>-Glycals
  作者：Mylène Richard、Claude Didierjean、Yves Chapleur、Nadia Pellegrini-Moïse

  DOI：10.1002/ejoc.201500130

  日期：2015.4

  for the base-mediated coupling with aromatic and primary thiols, which included 6-thio-sugars, cysteine derivatives, and glutathione. The success of the radical-mediated method depended on the thiol partners as well as the nature of the sugar olefins. Neither of the conditions required the protection of the sugar or the cysteine derivatives.

  在碱性和自由基条件下，对硫醇、硫糖和含硫醇的氨基酸和肽与三取代的活化异头糖烯烃的偶联进行了研究。氢硫醇化反应以区域和立体有择的方式发生，发生在异头中心，主要来自不太拥挤的面，即与 O-4 保护基团相反的方向。呋喃糖基和吡喃糖基亚基是与芳香族和伯硫醇（包括 6-硫代糖、半胱氨酸衍生物和谷胱甘肽）进行碱介导偶联的有价值的底物。自由基介导方法的成功取决于硫醇伙伴以及糖烯烃的性质。这两种情况都不需要保护糖或半胱氨酸衍生物。
• Tetrasubstituted C-Glycosylidenes and C-Glycosyl Compounds from Di- and Monobromo-Substituted exo-Glycals
  作者：Hoang-Trang Tran Thien、Alexandre Novoa、Nadia Pellegrini-Moïse、Françoise Chrétien、Claude Didierjean、Yves Chapleur

  DOI：10.1002/ejoc.201100949

  日期：2011.12

  Efficient methods for functionalization of readily available exo-glycals have been developed. Sequential palladium-catalysed cross-coupling of dibromo-substituted exo-glycals was first explored and allowed the formation of new disubstituted exo-glycals as single stereoisomers. Bromination of furano- and pyrano-methoxycarbonyl-exo-glycals led to a new series of monobrominated derivatives. These vinylic

  已经开发了用于容易获得的外-糖基官能化的有效方法。首次探索了连续钯催化的二溴取代外糖醇的交叉偶联，并允许形成新的双取代外糖醇作为单一立体异构体。呋喃-和吡喃-甲氧基羰基-exo-glycals 的溴化导致了一系列新的单溴化衍生物。这些乙烯基溴化物被用于通过钯催化反应形成碳-碳键，从而产生了一系列以前未知的外加糖。甲氧基羰基官能团的进一步化学操作和环外双键的立体选择性氢化导致具有高度立体控制的 C-糖基化合物。