(2R,3R,4S,5R)-2-(acetoxymethyl)-5-allyltetrahydrofuran-3,4-diyl diacetate | 106588-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R)-2-(acetoxymethyl)-5-allyltetrahydrofuran-3,4-diyl diacetate
• 英文别名: [(2R,3R,4S,5R)-3,4-diacetyloxy-5-prop-2-enyloxolan-2-yl]methyl acetate
• CAS: 106588-74-3
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: UVIHTBFXQVYMAR-YIYPIFLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R)-2-(acetoxymethyl)-5-allyltetrahydrofuran-3,4-diyl diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 4,7-anhydro-1,2,3-trideoxy-D-altro-oct-1-enitol
  参考文献：
  名称：

  [EN] 1'-ALKYL MODIFIED RIBOSE DERIVATIVES AND METHODS OF USE
  [FR] DÉRIVÉS DE RIBOSE MODIFIÉS PAR 1'-ALKYLE ET PROCÉDÉS D'UTILISATION

  摘要：

  The present disclosure provides linker compounds of Formula (I) or (II) pharmaceutically acceptable salts thereof, and related scaffolds and conjugates. More specifically, linker compounds of formulas (l-A), (Il-A) are provided: The present disclosure also relates to uses of the linker compounds, scaffolds, and conjugates, e.g., in delivering nucleic acid and/or treating or preventing diseases.

  公开号：

  WO2023014938A1
• 作为产物：
  描述：

  (3R,4R,5R)-2-Methoxy-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 水 作用下， 生成 (2R,3R,4S,5R)-2-(acetoxymethyl)-5-allyltetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  An efficient synthesis of anhydroalditols and allylic-glycosides

  摘要：

  DOI：

  10.1021/jo00381a030

文献信息

• Glycosamino Acids:  New Building Blocks for Combinatorial Synthesis
  作者：Jason P. McDevitt、Peter T. Lansbury

  DOI：10.1021/ja9525622

  日期：1996.4.24

  In order to produce inexpensive, chemically diverse carbohydrate building blocks more amenable for use in combinatorial organic synthesis, amine and carboxylic acid functional groups were incorporated into several monosaccharides. A series of 12 new glycosamino acids was prepared from commercially available starting materials. Conventional peptide synthesis solution coupling techniques were used to

  为了生产更适合用于组合有机合成的廉价、化学上多样化的碳水化合物结构单元，胺和羧酸官能团被加入到几种单糖中。一系列 12 种新的糖氨基酸是从市售的起始材料中制备的。传统的肽合成溶液偶联技术用于连接糖氨基酸，产生寡聚“糖苷”。最后，通过将糖氨基酸混合物偶联到刚性模板上产生糖苷库。
• Highly Stereoselective Glycosylation Reactions of Furanoside Derivatives via Rhenium (V) Catalysis
  作者：Emanuele Casali、Sirwan T. Othman、Ahmed A. Dezaye、Debora Chiodi、Alessio Porta、Giuseppe Zanoni

  DOI：10.1021/acs.joc.1c00706

  日期：2021.6.4

  approach for the formation of anomeric carbon-functionalized furanoside systems was accomplished through the employment of an oxo-rhenium catalyst. The transformation boasts a broad range of nucleophiles including allylsilanes, enol ethers, and aromatics in addition to sulfur, nitrogen, and hydride donors, able to react with an oxocarbenium ion intermediate derived from furanosidic structures. The excellent

  通过使用氧代铼催化剂，实现了一种形成异头碳官能化呋喃糖苷系统的新方法。该转变拥有广泛的亲核试剂，包括烯丙基硅烷、烯醇醚和芳烃以及硫、氮和氢化物供体，能够与源自呋喃糖苷结构的氧代碳鎓离子中间体反应。观察到的优异立体选择性遵循 Woerpel 模型，最终提供 1,3-顺式-1,4-反式系统。在富电子芳香亲核试剂的情况下，平衡发生在异头中心，选择性形成 1,3-反式-1,4-顺式系统。这个异常结果通过密度泛函理论计算得到了合理化。不同的氧代碳鎓离子，例如衍生自二氢异苯并呋喃、吡咯烷和恶唑烷杂环的那些，也可用作氧代-Re 介导的烯丙基化反应的底物。
• C-Glycosides of dodecanoic acid: new capping/reducing agents for glyconanoparticle synthesis
  作者：C.V. Ramana、Kulbhushan A. Durugkar、Vedavati G. Puranik、Sachin B. Narute、B.L.V. Prasad

  DOI：10.1016/j.tetlet.2008.08.030

  日期：2008.10

  A concise synthesis of 12-C-glycosylated dodecanoic acids employing an olefin cross-metathesis reaction is developed. Examination of these acids as capping agents for the synthesis of metal nanoparticles reveals that they do not cap the Co-metal nanoparticles synthesized in aqueous phase, but that two of them can reduce and cap the Ag nanoparticles in water without any aggregation. (C) 2008 Elsevier Ltd. All rights reserved.