2,5-anhydro-3,4:6,7-di-O-isopropylidene aldehydo-D-glycero-D-galacto-heptofuranose | 159722-71-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-3,4:6,7-di-O-isopropylidene aldehydo-D-glycero-D-galacto-heptofuranose
• 英文别名: (3aS,4R,6S,6aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carbaldehyde
• CAS: 159722-71-1
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: FYSCJLFMCZMMFE-ILAIQSSSSA-N

物化性质

• 沸点：
  351.0±42.0 °C(predicted)
• 密度：
  1.215±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,4:6,7-di-O-isopropylidene aldehydo-D-glycero-D-galacto-heptofuranose 在 palladium dihydroxide 六甲基磷酰三胺 、 正丁基锂 、 Amberlite IR-120 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 乙酸乙酯 为溶剂， -30.0~70.0 ℃ 、303.98 kPa 条件下， 反应 9.0h， 生成
  参考文献：
  名称：

  Synthesis of α- and β-d-(1→6)-C-Disaccharides by Wittig Olefination of Formyl C-Glycosides with Glycopyranose 6-Phosphoranes

  摘要：

  The synthesis of (1-->6)-C-disaccharides by Wittig condensation of formyl C-glycofuranosides and pyranosides with galacto-and glucopyranose B-phosphoranes is described herein. The method involves the coupling of the sugar aldehydes with the ylides and the reduction of the double bond of the resulting sugar alkenes, in most of the cases by catalytic hydrogenation. The reduction with nickel boride or diimide is employed in some special cases. O-Benzyl protective groups are removed by catalytic hydrogenation either in the course of the reduction of the double bond or in a subsequent step, while O-isopropylidene groups are cleaved by treatment with Amberlite IR-120. In this way, eight free beta-D-(1-->6)-C-disaccharides have been prepared in 26-61% overall yield starting from B-linked formyl C-glycosides. These include C-linked analogues of the biologically active disaccharides allolactose (Gal beta 1,6Glc), gentiobiose (Glc beta 1,6Glc), and N-acetylamino disaccharides (GalNHAc beta,6Gal and GalNHAc beta 1,6Glc). Moreover, the synthesis of two alpha-D-(1-->6)-C-disaccharides is described from formyl C-furanosides. The limiting condition of the synthesis of these stereoisomers is the configurational instability of the alpha-linked formyl C-glycosides under the basic conditions of the Wittig olefination.

  DOI：

  10.1021/jo971177n
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 samarium diiodide 、 乙二醇 、 三氟甲烷磺酸甲酯 、 mercury dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 2,5-anhydro-3,4:6,7-di-O-isopropylidene aldehydo-D-glycero-D-galacto-heptofuranose
  参考文献：
  名称：

  Synthesis of α- and β-d-(1→6)-C-Disaccharides by Wittig Olefination of Formyl C-Glycosides with Glycopyranose 6-Phosphoranes

  摘要：

  The synthesis of (1-->6)-C-disaccharides by Wittig condensation of formyl C-glycofuranosides and pyranosides with galacto-and glucopyranose B-phosphoranes is described herein. The method involves the coupling of the sugar aldehydes with the ylides and the reduction of the double bond of the resulting sugar alkenes, in most of the cases by catalytic hydrogenation. The reduction with nickel boride or diimide is employed in some special cases. O-Benzyl protective groups are removed by catalytic hydrogenation either in the course of the reduction of the double bond or in a subsequent step, while O-isopropylidene groups are cleaved by treatment with Amberlite IR-120. In this way, eight free beta-D-(1-->6)-C-disaccharides have been prepared in 26-61% overall yield starting from B-linked formyl C-glycosides. These include C-linked analogues of the biologically active disaccharides allolactose (Gal beta 1,6Glc), gentiobiose (Glc beta 1,6Glc), and N-acetylamino disaccharides (GalNHAc beta,6Gal and GalNHAc beta 1,6Glc). Moreover, the synthesis of two alpha-D-(1-->6)-C-disaccharides is described from formyl C-furanosides. The limiting condition of the synthesis of these stereoisomers is the configurational instability of the alpha-linked formyl C-glycosides under the basic conditions of the Wittig olefination.

  DOI：

  10.1021/jo971177n

文献信息

• ‘In situ’ Generated ‘HCl’ - An Efficient Catalyst for Solvent-Free Hantzsch Reaction at Room Temperature: Synthesis of New Dihydropyridine Glycoconjugates
  作者：G. V. Sharma、K. Laxmi Reddy、P. Sree Lakshmi、Palakodety Radha Krishna

  DOI：10.1055/s-2005-921744

  日期：——

  HCl, generated in situ from 2,4,6-trichloro[1,3,5]triazine (TCT, cyanuric chloride), catalyzed a solvent free Hantzsch reaction at room temperature with enhanced reaction rates. The reaction conditions allow facile preparation of glycoconjugates of dihydropyridines under mild reaction conditions in high yields.

  由2,4,6-三氯[1,3,5]三嗪（TCT，氰尿酰氯）原位生成的HCl，在室温下催化了一项无溶剂的Hantzsch反应，并显著提高了反应速率。该反应条件使得在温和的反应条件下，能够以高产率便捷地制备二氢吡啶的糖共轭物。
• Stereoselective synthesis of new dihydropyrimidinone glycoconjugates #
  作者：G. V. M. Sharma、K. Laxmi Reddy、P. Sree Lakshmi、Palakodety Radha Krishna

  DOI：10.1002/jhet.5570420719

  日期：2005.11

  Stereoselective synthesis of dihydropyrimidinone glycoconjugates in high yields, from different sugar aldehydes, by a three-component coupling (Biginelli) reaction is reported. In this new method, HC1 generated ‘in situ’ from2,4,6-trichloro[l,3,5]triazine(TCT; 10 mol%), was used under mild and solvent free reaction conditions.

  据报道，通过三组分偶联（Biginelli）反应，可以从不同的糖醛高产率地立体选择性合成二氢嘧啶酮糖缀合物。在这种新方法中，由2,4,6-三氯[1,3,5]三嗪（TCT； 10 mol％）“原位”生成的HCl在温和且无溶剂的反应条件下使用。
• A Versatile Protocol for theSynthesis of Oxazole and 3-Nitro/3-Carbethoxy Pyrrole<i>C</i>-Nucleosides using TOSMIC
  作者：Palakodety Radha Krishna、Vuyyuru V. Reddy、Gangavaram V. Sharma

  DOI：10.1055/s-2003-41007

  日期：——

  The synthesis of oxazole and pyrrole C-nucleosides usingTOSMIC in moderate to good yields is reported.

  据报道，使用 TOSMIC 以中等至良好的产率合成恶唑和吡咯 C-核苷。
• Stereoselective synthesis of C1–C5 and C4–C5 linked deoxy disaccharides via a ring closing metathesis protocol
  作者：G.V.M. Sharma、Asra Begum、K. Raman Kumar、Palakodety Radha Krishna、A. Prabhakar、A.C. Kunwar

  DOI：10.1016/j.tetlet.2005.03.103

  日期：2005.6

  The stereoselective synthesis of C–C linked deoxy disaccharides by a short and efficient route is described. An RCM strategy was adopted for the assembly of the required ring skeleton on the sugar unit, while OsO4 was used to introduce the vic-diol unit.

  描述了通过短而有效的途径进行的C–C连接的脱氧二糖的立体选择性合成。采用RCM策略在糖单元上组装所需的环骨架，同时使用OsO 4引入vic-二醇单元。
• Steric determinants in diastereocontrol during Baylis–Hillman reaction of sugar-derived aldehydes
  作者：Palakodety Radha Krishna、A. Manjuvani、V. Kannan

  DOI：10.1016/j.tetasy.2005.06.026

  日期：2005.8

  Diastereoselective Baylis-Hillman reaction using different sugar-derived aldehydes with various activated olefins afforded chiral multifunctional adducts in good yields. Steric factors that dictate and determine the diastereoselection will be discussed. (c) 2005 Elsevier Ltd. All rights reserved.