methyl (2Z)-2-[(3aR,6R,6aR)-6-(methoxymethoxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ylidene]acetate | 679436-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2Z)-2-[(3aR,6R,6aR)-6-(methoxymethoxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ylidene]acetate
• CAS: 679436-89-6
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: OPELPGZXVVEGDI-RCZLXPMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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 (2Z)-2-[(3aR,6R,6aR)-6-(methoxymethoxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ylidene]acetate 在 palladium on activated charcoal 二苯基膦叠氮化物 、 氢气 、 potassium carbonate 、 三乙胺 、 苄胺 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 51.0h， 生成 [2R,3R,4R,5R,8S]-2-[(methoxymethoxy)methyl]-3,4-isopropylidenedioxy-8-methyl-1-oxa-6,9-diazaspiro-[4,6]-undecan-7,10-dione
  参考文献：
  名称：

  异头spiroannelated 1,4-二氮杂卓从呋喃-2,5-二酮外-glycals：迈向一个新的类spironucleosides的

  摘要：

  描述了包含β-氨基酸的1，4-二氮杂2，5-二酮肽的第一合成，其中β碳也是呋喃糖的异头碳。在d- gulo，d- manno，d- allo和d- ribo系列中通过立体选择性控制获得的这些新的异头螺旋糖可被视为新型螺核苷的首批成员。在我们的研究过程中，还分离了包含两个相同的糖β-氨基酸和α-氨基酸残基的两个对称的四聚环肽，这些结构可能作为新的潜在宿主分子而受到关注。

  DOI：

  10.1016/j.tet.2004.01.030
• 作为产物：
  描述：

  2,3-O-(1-methylethylidene)-5-O-methoxymethyl-D-ribonic acid γ-lactone 、 甲氧羰基亚甲基三苯基正膦 以 甲苯 为溶剂， 反应 17.0h， 生成 methyl (2E)-2-[(3aR,6R,6aR)-6-(methoxymethoxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ylidene]acetate 、 methyl (2Z)-2-[(3aR,6R,6aR)-6-(methoxymethoxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ylidene]acetate
  参考文献：
  名称：

  异头spiroannelated 1,4-二氮杂卓从呋喃-2,5-二酮外-glycals：迈向一个新的类spironucleosides的

  摘要：

  描述了包含β-氨基酸的1，4-二氮杂2，5-二酮肽的第一合成，其中β碳也是呋喃糖的异头碳。在d- gulo，d- manno，d- allo和d- ribo系列中通过立体选择性控制获得的这些新的异头螺旋糖可被视为新型螺核苷的首批成员。在我们的研究过程中，还分离了包含两个相同的糖β-氨基酸和α-氨基酸残基的两个对称的四聚环肽，这些结构可能作为新的潜在宿主分子而受到关注。

  DOI：

  10.1016/j.tet.2004.01.030

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。
• Cycloaddition reactions on activated exo-glycals
  作者：Gérald Enderlin、Claude Taillefumier、Claude Didierjean、Yves Chapleur

  DOI：10.1016/j.tetasy.2005.06.027

  日期：2005.7

  Cycloaddition reactions of activated exo-glycals and nitrones proceeded only under microwave activation, with excellent facial selectivities on furanoglycosylidenes and good stereocontrol on the nitrone producing only two diastereomeric spiroisoxazolidines. alpha/beta-Spiro sugar-isoxazolidines are obtained from pyrano exo-glycals. The cycloaddition reaction with nitrile oxide proceeds at room temperature and gives open-chain isoxazoles due to facile beta-elimination of the sugar ring oxygen on the intermediate isoxazoline ring system. All the heterocycles obtained this way can be regarded as nucleoside analogues. (C) 2005 Elsevier Ltd. All rights reserved.
• Spiro sugar-isoxazolidine scaffold as useful polyfunctional building block for peptidomimetics design
  作者：Mylène Richard、Yves Chapleur、Nadia Pellegrini-Moïse

  DOI：10.1016/j.carres.2016.01.005

  日期：2016.3

  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.
• Anomeric spiroannelated 1,4-diazepine 2,5-diones from furano exo-glycals: towards a new class of spironucleosides
  作者：Claude Taillefumier、Sabine Thielges、Yves Chapleur

  DOI：10.1016/j.tet.2004.01.030

  日期：2004.3

  The first synthesis of 1,4-diazepine 2,5-dione peptides containing a β-amino acid in which the β carbon is also the anomeric carbon of a furanoid sugar is described. These new anomeric spirosugars obtained with a stereoselective control in the d-gulo, d-manno, d-allo and d-ribo series can be regarded as the first members of a new class of spironucleosides. In the course of our study, two symmetrical

  描述了包含β-氨基酸的1，4-二氮杂2，5-二酮肽的第一合成，其中β碳也是呋喃糖的异头碳。在d- gulo，d- manno，d- allo和d- ribo系列中通过立体选择性控制获得的这些新的异头螺旋糖可被视为新型螺核苷的首批成员。在我们的研究过程中，还分离了包含两个相同的糖β-氨基酸和α-氨基酸残基的两个对称的四聚环肽，这些结构可能作为新的潜在宿主分子而受到关注。