(1R,2R,5R)-2-(dimethoxymethyl)-3,6-dioxabicyclo[3.1.0]hexane | 89860-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: (1R,2R,5R)-2-(dimethoxymethyl)-3,6-dioxabicyclo[3.1.0]hexane
• 英文别名: (2R,3R,4R)-2-dimethoxymethyl-3,4-epoxytetrahydrofuran；3,4-epoxy-5-(R,R)-dimethoxymethyltetrahydrofuran
• CAS: 89860-19-5
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: OYLUINIYPUWQBD-HSUXUTPPSA-N

物化性质

• 沸点：
  225.4±30.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,5R)-2-(dimethoxymethyl)-3,6-dioxabicyclo[3.1.0]hexane 在 sodium tetrahydroborate 、 草酰氯 、 二异丁基氢化铝 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 6.0h， 生成 (2R,3S)-2-(dimethoxymethyl)oxolan-3-ol
  参考文献：
  名称：

  母体顺式和反式呋喃类β-氨基酸的手性均聚物的合成与结构表征

  摘要：

  进行了顺式和反式-3-氨基四氢呋喃-2-羧酸（母体顺式和反式呋喃酮-β-氨基酸，称为“顺式/反式FAA”）的同手性均聚物的合成了解它们的二级结构及其对环杂原子的依赖性。两种非对映异构体的寡聚体已显示出独特的左旋螺旋度。所述顺-FAA均-寡聚物显示出14螺旋结构，在对比的均-寡聚物顺-ACPC来说，在采用像结构的薄片。该反式发现FAA均聚物采用12螺旋结构，与反式ACPC均聚物的趋势相同。借助于从头算，比较了顺式ACPC和顺式FAA六聚体的结构特征。我们认为，顺式-FAA六肽的堆积更为紧凑，这应归因于环与主链酰胺氢之间更有利的相互作用。

  DOI：

  10.1002/chem.201101855
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (1R,2R,5R)-2-(dimethoxymethyl)-3,6-dioxabicyclo[3.1.0]hexane
  参考文献：
  名称：

  Synthesis of some pyrrolo[2,3-d]pyrimidine and 1,2,3-triazole isonucleosides

  摘要：

  Nucleoside analogues 8, 9, 10 and 11, in which a pyrrolo[23-d]pyrimidine ring is linked to a 2-hydroxymethyl-3-hydroxytetrahydrofuran, have been prepared. The azide 16 used as an intermediate in the routes to these compounds also gave access to the 1, 2, 3-triazole isonucleosides 12 and 13. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00102-6

文献信息

• Synthesis of Cyclic γ-Amino Acids for Foldamers and Peptide Nanotubes
  作者：Nuria Rodríguez-Vázquez、Stephan Salzinger、Luis F. Silva、Manuel Amorín、Juan R. Granja

  DOI：10.1002/ejoc.201201565

  日期：2013.6

  Cyclic γ-amino acids are molecular building blocks of great interest in peptide and foldamer chemistry, as they allow the preparation of new structures that are not found in Nature. In this paper, we describe the synthesis of cyclic γ-amino acids that have a cis relationship between the amino and the carboxylic acid groups. This arrangement, in most cases, induces the resulting peptides to adopt a

  环状γ-氨基酸是肽和折叠体化学中非常受关注的分子构建块，因为它们允许制备自然界中未发现的新结构。在本文中，我们描述了在氨基和羧酸基团之间具有顺式关系的环状 γ-氨基酸的合成。在大多数情况下，这种排列会导致生成的肽采用扁平构象，这使得它们适用于采用 β-折叠型结构的折叠体的设计。
• A remarkable chiral recognition of racemic Mosher's acid salt by naturally derived chiral ionic liquids using ¹⁹F NMR spectroscopy
  作者：R. Jayachandra、Sabbasani Rajasekhara Reddy

  DOI：10.1039/c6ra02792j

  日期：——

  A new class of D-xylose derived imidazolium-based chiral ionic liquids were designed and synthesized via simple tuning approaches. The developed chiral ionic liquids were tested for their chiral recognition properties with racemic Mosher's acid salt using 19F NMR spectroscopy. For the first time, we demonstrate the excellent enantioselective discrimination of the racemic salt using significantly less

  通过简单的调节方法，设计并合成了一类新型的D-木糖衍生的咪唑鎓基手性离子液体。使用19 F NMR光谱，用外消旋Mosher酸盐测试了开发的手性离子液体的手性识别性能。首次，我们证明了使用明显更少当量的碳水化合物衍生的手性离子液体对消旋盐具有出色的对映选择性。我们已经使用19 F NMR光谱确定了Mosher酸盐的非外消旋混合物的对映体过量值。
• An efficient and convenient formal synthesis of Jaspine B from d-xylose
  作者：Ming-Li Zhao、En Zhang、Jie Gao、Zhao Zhang、Yu-Tao Zhao、Wen Qu、Hong-Min Liu

  DOI：10.1016/j.carres.2012.01.013

  日期：2012.4

  A formal synthesis of Jaspine B was completed in 42.4% overall yield with only three purification steps (one by crystallization and two by column chromatography). The key step in the synthesis involves a regio- and stereoselective epoxide ring-opening reaction and the configuration inversion of the C3-hydroxyl group through oxidation and reduction. All of the reagents and materials used were quite common and inexpensive. (C) 2012 Elsevier Ltd. All rights reserved.
• Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines
  作者：Hong-Wu Yu、Liang-Ren Zhang、Ji-Chang Zhou、Ling-Tai Ma、Li-He Zhang

  DOI：10.1016/0968-0896(96)00048-x

  日期：1996.4

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of 5-substituted-3-[(2′ S ,3′ S )-3′-hydroxy-2′-hydroxymethyltetrahydrofuran-3′-yl]-1,2,4-oxadiazoles and their epimers
  作者：W.D Wu、L.T Ma、L.H Zhang、Y Lu、F Guo、Q.T Zheng

  DOI：10.1016/s0957-4166(00)00095-1

  日期：2000.4

  5-Phenyl-3-[(2' R,3'S)-3'-hydroxy-2'-dimethoxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazole 10a and its epimer 11a, 5-methyl-3-[(2' R,3' S)-3'-hydroxy-2'-dimethoxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazole 10b and its epimer 11b were synthesized from cyanohydrin benzoates 8a, 9a and cyanohydrin acetates 8b, 9b, respectively, by treatment with hydroxylamine in methanol via intramolecular transacylation and subsequent cyclization of the corresponding amidoximes. Hydrolysis and reduction of the dimethoxymethyl groups in the above compounds gave the desired compounds 12a, 13a, 12b and 13b, (C) 2000 Elsevier Science Ltd. All rights reserved.