2,3-O-isopropylidene-L-rhamnofuranose | 112245-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-L-rhamnofuranose
• 英文别名: 6-Deoxy-2,3-O-isopropyliden-L-mannofuranose；2,3-O-Isopropyliden-L-rhamnose；(3aR,6S,6aR)-6-[(1S)-1-hydroxyethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• CAS: 112245-58-6
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: ICBGDXBFVVCSND-QKVVPUOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-L-rhamnofuranose 在 溶剂黄146 、 三氟乙酸 作用下， 反应 42.0h， 生成 7-deoxy-L-glycero-L-galacto-heptono-1,4-lactone
  参考文献：
  名称：

  Ketals of L-rhamnoheptonolactones: Potential mimics of L-rhamnose

  摘要：

  Isopropylidene and cyclohexylidene ketals of gamma- and delta-heptonolactones derived from Kiliani ascensions of protected L-rhamnose may constitute suitable intermediates for the preparation of mimics of L-rhamnose. The X-ray crystal structure of 7-deoxy-3,4-O-isopropylidene-1-glycero-1-galacto-hepta 1,5-lactone provides an example of a delta-lactone in a boat conformation with a substituent in a flagpole position. The size of ring in the lactones is completely consistent with Hudson's classical lactone rotation rule of 1910.

  DOI：

  10.1016/s0957-4166(00)80399-7
• 作为产物：
  描述：

  L-鼠李糖 在 sulfonated graphene catalyst 作用下， 以90 %的产率得到2,3-O-isopropylidene-L-rhamnofuranose
  参考文献：
  名称：

  磺化石墨烯（GR-SO3H）作为可持续酸催化剂催化高效制备碳水化合物的邻异丙叉衍生物

  摘要：

  磺化石墨烯（GR-SO3H）已成为一种温和、高效且可持续的催化剂，用于制备室温下，未保护和异头保护的碳水化合物与丙酮和 2,2-二甲氧基丙烷的 O-异丙叉衍生物。该方法不仅提供了优异的产率，还缩短了反应时间，并且表现出出色的可回收性，允许催化剂多次重复使用。

  DOI：

  10.1055/a-2218-7604

文献信息

• Sulfuric acid immobilized on silica: an efficient reusable catalyst for the synthesis of O-isopropylidene sugar derivatives
  作者：Vishal Kumar Rajput、Balaram Mukhopadhyay

  DOI：10.1016/j.tetlet.2006.06.050

  日期：2006.8

  Sulfuric acid immobilized on silica proved to be an efficient catalyst for the synthesis of O-isopropylidene sugar derivatives from reducing sugars. The method is very simple and economic for large-scale synthesis in which the catalyst is recovered and reused several times. Reactions with d-glucose, d-galactose, d-mannose, l-rhamnose, l-arabinose, d-xylose and l-sorbose led to the formation of the corresponding

  固定在二氧化硅上的硫酸被证明是从还原糖合成O-异亚丙基糖衍生物的有效催化剂。该方法对于大规模合成非常简单且经济，其中催化剂被回收并重复使用多次。与d-葡萄糖，d-半乳糖，d-甘露糖，l-鼠李糖，l-阿拉伯糖，d-木糖和l-山梨糖的反应导致形成相应的热力学稳定的二-O-和/或单-O-异亚丙基衍生品，收益率高至优。
• A simple and convenient synthetic protocol for O-isopropylidenation of sugars using bromodimethylsulfonium bromide (BDMS) as a catalyst
  作者：Abu T. Khan、Md. Musawwer Khan

  DOI：10.1016/j.carres.2009.09.017

  日期：2010.1

  Various O-isopropylidene derivatives of sugars and acyclic sugars were obtained in very good yields on reaction with acetone at room temperature with a catalytic amount of bromodimethylsulfonium bromide (BDMS). These O-isopropylidene derivatives can also be prepared in good yields on reaction with 2,2-dimethoxypropane (DMP) in acetonitrile using the same catalyst in shorter reaction times. Some of

  在室温下与丙酮和催化量的溴二甲基s溴化物（BDMS）反应后，可以以非常高的收率获得糖和无环糖的各种O-异亚丙基衍生物。这些O-异亚丙基衍生物也可以在较短的反应时间内使用相同的催化剂与乙腈中的2,2-二甲氧基丙烷（DMP）反应，以高收率制备。该方法的一些优点是高效，非水后处理程序，经济可行性和良好的产率。
• Acetonation of l-pentoses and 6-deoxy-l-hexoses under kinetic control using heterogeneous acid catalysts
  作者：Jonas J. Forsman、Reko Leino

  DOI：10.1016/j.carres.2010.05.002

  日期：2010.7

  H+ proved to be an efficient catalyst for the preparation of O-isopropylidene derivatives from a series of rare sugars. Acetonation of the reducing sugars L-arabinose, L-ribose, L-xylose, L-fucose, and L-rhamnose in N,N-dimethylformamide by 2,2-dimethoxypropane or 2-methoxypropene led to the formation of the kinetically favored di-O- and/or mono-O-isopropylidene derivatives in 46-88% yields. The method

  纤维状聚合物负载的磺酸催化剂Smopex-101 H +被证明是从一系列稀有糖中制备O-异亚丙基衍生物的有效催化剂。N，N-二甲基甲酰胺中的还原糖L-阿拉伯糖，L-核糖，L-木糖，L-岩藻糖和L-鼠李糖的乙酰化作用是由2,2-二甲氧基丙烷或2-甲氧基丙烯引起的-O-和/或单-O-异亚丙基衍生物，产率为46-88％。该方法由简单的实验程序组成，不需要预先干燥的溶剂或试剂。该催化剂易于回收并且可以再生，从而使得该方法即使对于大规模合成也在经济上可行。
• SUBSTITUTED NUCLEOTIDE ANALOGS
  申请人：Beigelman Leonid

  公开号：US20120070411A1

  公开（公告）日：2012-03-22

  Disclosed herein are phosphoroamidate nucleotide analogs, methods of synthesizing phosphoroamidate nucleotide analogs and methods of treating diseases and/or conditions such as viral infections, cancer, and/or parasitic diseases with the phosphoroamidate nucleotide analogs.

  本文揭示了磷酰胺核苷类似物、合成磷酰胺核苷类似物的方法以及使用磷酰胺核苷类似物治疗病毒感染、癌症和/或寄生虫病等疾病和/或病况的方法。
• Organoiridium complexes: efficient catalysts for the formation of sugar acetals and ketals
  作者：Soumik Mandal、Prashant Ranjan Verma、Balaram Mukhopadhyay、Parna Gupta

  DOI：10.1016/j.carres.2011.05.008

  日期：2011.9

  [Cp*IrCl2](2) is used as an efficient promoter for the synthesis of sugar acetals and ketals with good to excellent yields. The catalyst is found to be general for a wide range of sugars. (C) 2011 Elsevier Ltd. All rights reserved.