3,4:5,6-di-O-isopropylidene-D-glucose | 161721-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4:5,6-di-O-isopropylidene-D-glucose
• 英文别名: (2R)-2-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetaldehyde
• CAS: 161721-25-1
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: YNWNUISOPSCDAQ-SGIHWFKDSA-N

物化性质

• 沸点：
  338.9±42.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4:5,6-di-O-isopropylidene-D-glucose 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (S)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethane-1,2-diol
  参考文献：
  名称：

  New Access to 1-Deoxynojirimycin Derivatives via Azide−Alkene Cycloaddition

  摘要：

  The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-delta-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.

  DOI：

  10.1021/ol8014495
• 作为产物：
  描述：

  1,2:3,4:5,6-tri-O-isopropylidene-δ-gluconolactone 在 二异丁基氢化铝 、 三乙胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 3.0h， 生成 3,4:5,6-di-O-isopropylidene-D-glucose
  参考文献：
  名称：

  Jarosz, S.; Kozlowska, E.; Ciunik, Z., Polish Journal of Chemistry, 1994, vol. 68, # 11, p. 2209 - 2216

  摘要：

  DOI：

文献信息

• Synthesis of Sugar-Derived 2′- and 3′-Substituted Furans and Their Application in Diels−Alder Reactions
  作者：Sławomir Jarosz、Mateusz Mach、Katarzyna Szewczyk、Stanisław Skóra、Zbigniew Ciunik

  DOI：10.1002/1099-0690(200108)2001:15<2955::aid-ejoc2955>3.0.co;2-0

  日期：2001.8

  A convenient synthesis of 2′- and 3′-furyl sugars in which the furan and the sugar parts are directly connected is presented. The key step comprises HF·py-induced cyclization of α,β-unsaturated carbonyl compounds (ketones or aldehydes) possessing terminal hydroxymethylene groups protected as TBDPS ethers. Treatment of such furan derivatives with N-phenylmaleimide under high-pressure conditions (11

  提出了一种2'-和3'-呋喃糖的便捷合成方法，其中呋喃和糖部分直接相连。关键步骤包括HF·py诱导的具有被保护为TBDPS醚的末端羟基亚甲基的α，β-不饱和羰基化合物（酮或醛）的环化反应。在高压条件下（11 kbar）用N-苯基马来酰亚胺处理此类呋喃衍生物可生成相应的[4 + 2]加合物，其中内型占主导。然而，在p = 1 atm和T = 20°C时，形成了exo异构体作为主要产物。[4 + 2]加合物在升高的温度和大气压下进行逆狄尔斯-阿尔德反应。
• Application of stabilized sugar-derived phosphoranes in the synthesis of higher carbon monosaccharides. First synthesis of a C21-dialdose
  作者：Slawomir Jarosz、Piotr Salanski、Mateusz Mach

  DOI：10.1016/s0040-4020(98)00021-0

  日期：1998.3

  aldehyde 1 with C9 stabilized phosphoranes 2 and 3 respectively. The “smaller” C19 sugar 13 was prepared from a C12 aldehyde 1 and C7 phosphorane 4. All reactions with phosphoranes were performed under high pressure (13 kbar). No reaction was observed under normal pressure even at high temperature (ca 140°C). The synthesis of C19 and C21 monosaccharides was accomplished also under normal pressure when phosphoranes

  C 21单糖前体11和12分别通过C 12醛1与C 9稳定的膦烷2和3的偶联而合成。在“较小” C 19糖13是从C中制备12醛1和C 7正膦4。与磷烷的所有反应均在高压（13 kbar）下进行。即使在高温（约140℃）下，在常压下也未观察到反应。C 19和C的合成当磷烷被更多的亲核性膦酸酯替代时，在常压下也可以完成21种单糖。然而，与高级糖烯酮11、12和13一起分离出部分消除的产物（M-苄醇）。糖α-羟基醛（14）即使在13kbar的压力下也不会与C 9-膦烷反应，尽管与更短的类似物-C 7磷烷15的反应是在常压下在沸腾的苯中进行的。
• A convenient route to enantiomerically pure highly oxygenated decalins from sugar allyltin derivatives
  作者：Sławomir Jarosz、Stanisław Skóra

  DOI：10.1016/s0957-4166(00)00084-7

  日期：2000.4

  Preparation of enantiomerically pure, highly oxygenated decalins via tandem Wittig-type Diels–Alder reactions from the corresponding sugar-derived dieno-phosphoranes and/or -phosphonates and sugar aldehydes is described. Application of the phosphonates is more convenient than phosphoranes since the former can be prepared in much higher yields and react with aldehydes under milder conditions. The intermediate

  描述了通过串联的Wittig型Diels-Alder反应从相应的糖衍生的二膦基膦酸酯和/或-膦酸酯和糖醛制备对映体纯的，高度氧化的十氢化萘。膦酸酯的施用比磷烷更方便，因为前者可以更高的产率制备，并在温和的条件下与醛反应。在反应条件下，由Wittig-型方法产生的中间体三烯自发且高度立体选择性地环化为顺式-十氢化萘。
• Tandem Wittig–Diels–Alder reaction between sugar-derived phosphoranes and sugar aldehydes. An easy route to optically pure highly oxygenated decalins
  作者：Sławomir Jarosz

  DOI：10.1039/a707447f

  日期：——

  A highly oxygenated decalin system has been obtained by a tandem Wittig–Diels–Alder reaction of sugar derived phosphoranes with sugar aldehydes.

  通过糖源磷烯与糖醛的串联Wittig-Diels-Alder反应，获得了一种高度氧化的二氢萘系统。
• Zinc mediated deoxygenation of 4-hydroxy-2-butenoic acid moiety. An application for the synthesis of multifunctional chiral synthon
  作者：J.S Yadav、D.K Barma

  DOI：10.1016/0040-4020(96)00093-2

  日期：1996.3

  A facile and practical method for the deoxygenation of 4-alkoxy-2-butenoic acid moiety mediated by zinc is described to prepare multifunctional chiral building blocks from carbohydrates and tartaric acid.

  描述了由锌介导的4-烷氧基-2-丁烯酸部分脱氧的简便实用方法，以由碳水化合物和酒石酸制备多功能手性结构单元。