octyl 2,3,5-tri-O-benzyl-β-D-galactofuranoside | 189315-16-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 2,3,5-tri-O-benzyl-β-D-galactofuranoside
• 英文别名: (2R)-2-[(2S,3S,4R,5R)-5-octoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]-2-phenylmethoxyethanol
• CAS: 189315-16-0
• 化学式: C₃₅H₄₆O₆
• 分子量: 562.747
• InChiKey: CTBOSVJLSVEUAU-NDFHSCBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  41
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  octyl 2,3,5-tri-O-benzyl-β-D-galactofuranoside 在 palladium diacetate 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 硫酸 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 128.0h， 生成 L-Galactofuranose, 6-deoxy-, tetraacetate
  参考文献：
  名称：

  使用未保护的1-硫代亚氨酰基六呋喃糖苷的一步法合成游离的呋喃呋喃糖基1-磷酸盐

  摘要：

  从新的未保护的糖呋喃糖基供体开始，开发了用于合成呋喃糖基1-磷酸酯的一般的一步策略。它首先需要制备带有硫代酰亚胺基杂环作为离去基团的新的1-硫己呋喃呋喃糖苷。硫和/或氮原子（一个或多个）上的糖苷配基的存在使得这些thioglycofuranosides的远程激活通过无水磷酸，并导致目标磷酸盐9，27，29，和30具有良好的选择性至极好的选择性，更重要的是，环扩展非常有限或没有。此外，通过避免对带负电荷的化合物进行任何繁琐的保护基操作并着重于简单但通用的纯化程序，可以显着改善这一一步的磷酸化反应。该方法被用于d-半乳糖和d-呋喃呋喃糖基1-磷酸的非对映控制合成，还用于制备稀有的差向异构体和/或脱氧对应物，即d-甘露糖醛和d-呋喃呋喃糖基衍生物。

  DOI：

  10.1021/jo0484934
• 作为产物：
  描述：

  octyl β-D-galactofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 水 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.25h， 生成 octyl 2,3,5-tri-O-benzyl-β-D-galactofuranoside
  参考文献：
  名称：

  含有呋喃糖苷单元的二糖的便捷合成

  摘要：

  摘要通过氯化铁促进4-戊烯-1-醇与d-葡萄糖的一锅反应，合成了Pent-4-enyl 2,3,5,6-tetra-O-acetyl- d-糖呋喃糖苷。 ，分别在异质培养基中添加d-甘露糖和d-半乳糖，然后进行原位乙酰化。这些正戊烯基糖苷是有效的呋喃呋喃糖基供体，因此已用于随后合成与古细菌糖脂和原生动物糖缀合物有关的各种呋喃糖基-吡喃糖苷型或呋喃糖基-呋喃糖苷型二糖。

  DOI：

  10.1016/s0008-6215(96)00268-6

文献信息

• Synthesis and Reactions of 1,4-Anhydrogalactopyranose and 1,4-Anhydroarabinose - Steric and Electronic Limitations
  作者：Toshiki Nokami、Daniel B. Werz、Peter H. Seeberger

  DOI：10.1002/hlca.200590224

  日期：2005.11

  Scope and limitations of 1,4-anhydro sugars as precursors of glycofuranosyl building blocks are described. The experiments revealed that the choice of the substituents is very important for an efficient preparation as well as a successful ring-opening reaction of 1,4-anhydro sugars. DFT Calculations suggest that selective protonation of 1,4-anhydro sugars is the key to the selective ring opening in

  描述了1，4-脱水糖作为呋喃呋喃糖基结构单元前体的范围和局限性。实验表明，取代基的选择对于有效制备以及成功地进行1,4-脱水糖的开环反应非常重要。DFT计算表明，1,4-脱水糖的选择性质子化是仅提供呋喃糖苷的选择性开环的关键。
• A Chemoenzymatic Approach for the Synthesis of Unnatural Disaccharides ContainingD-Galacto- orD-Fucofuranosides
  作者：Ronan Euzen、Gérald Lopez、Caroline Nugier-Chauvin、Vincent Ferrières、Daniel Plusquellec、Caroline Rémond、Michael O’Donohue

  DOI：10.1002/ejoc.200500525

  日期：2005.11

  substrates were then used in AbfD3-catalysed hydrolyses to determine the parameters Km and kcat and in AbfD3-catalysed transglycosylation to evaluate their ability to serve as donor/acceptor. Four disaccharides were thus isolated and characterised, two resulting from -(1,2) connection along with two -(1,3)-regioisomers.

  由 D-呋喃己糖基实体组成的不寻常二糖苷是通过化学酶途径使用 -L-阿拉伯呋喃糖苷酶 AbfD3 制备的。首先根据多步合成制备所需的未保护单糖供体。由于本研究的一个目标是研究酶活性位点中的供体 -1 亚位点，因此我们专注于 D-fucofuranosyl 和 6-deoxy-6-fluoro-D-galactofuranosyl 衍生物，它们与 L-阿拉伯糖系列具有立体化学相似性，还有侧臂的结构变化。然后将这些底物用于 AbfD3 催化的水解以确定参数 Km 和 kcat，并用于 AbfD3 催化的转糖基化以评估它们作为供体/受体的能力。因此分离并表征了四种二糖，其中两种来自 -(1,2) 连接以及两种 -(1,
• Synthesis of galactofuranose-containing disaccharides using thioimidoyl-type donors
  作者：Ronan Euzen、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1016/j.carres.2006.10.001

  日期：2006.12

  Four galactofuranose-containing disaccharides have been prepared utilising various thioimidates [Galf-SC(=NR)XR'] and suitably protected acceptors as key precursors. We observed that the efficiency of the coupling reactions was particularly dependent on the aglycon present on the furanosyl donor when copper(II) ions were used as the promoter, and that activation could be correlated with the nature of the third heteroatorn, X. (c) 2006 Elsevier Ltd. All rights reserved.
• A facile method for deprotection of trityl ethers using column chromatography
  作者：Ashish K Pathak、Vibha Pathak、Lainne E Seitz、Kamal N Tiwari、Mohammad S Akhtar、Robert C Reynolds

  DOI：10.1016/s0040-4039(01)01645-8

  日期：2001.10

  A mild, efficient and inexpensive detritylation method is reported that uses trifluoroacetic acid on a silica gel column to obtain pure, detritylated compounds in one-step. This method is applicable to acid stable as well as acid sensitive compounds with only slight alterations in the procedure. Nineteen examples are given. (C) 2001 Elsevier Science Ltd. All rights reserved.
• First <i>O</i>-Glycosylation from Unprotected 1-Thioimidoyl Hexofuranosides Assisted by Divalent Cations
  作者：Ronan Euzen、Jean-Paul Guégan、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1021/jo070741j

  日期：2007.7.1

  The preparation of O-hexofuranosides was accomplished from unprotected 1-thioimidoyl furanosides as donors. The present methodology was first used for the synthesis of octyl galactofuranoside and further extended to D-galactofuranose-containing disaccharides. Within this study, we emphasized the need for additional complexing cations to maintain the furanose ring in its initial size. After experimentation, calcium ion was first used concomitantly with trimethylsilyl trifluoromethanesulfonate, the latter being able to activate the thioimidate and the former being likely to inhibit ring expansion. Moreover, an improvement was performed by using copper(II) trifluoromethanesulfonate which could then meet the requirements as both promoter and complexing agent.