2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone | 123765-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone
• 英文别名: [(2S,3S,4R)-4-benzoyloxy-2-[(1R)-1-benzoyloxy-2-hydroxyethyl]-5-oxooxolan-3-yl] benzoate
• CAS: 123765-15-1
• 化学式: C₂₇H₂₂O₉
• 分子量: 490.466
• InChiKey: MXUWXETVEYQRTG-WZYRSQIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 mercury dibromide 、 mercury(II) oxide molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以50%的产率得到3,4,6-tri-O-acetyl-1,2-O-<1(S)-(2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone-6-yloxy)ethylidene>-α-D-glucopyranose
  参考文献：
  名称：

  一种以呋喃糖为还原单元的二糖衍生物合成的新方法

  摘要：

  摘要内酯二糖2,3,5-三-O-苯甲酰基-6-O-（2,3,4,6-四-O-乙酰基-β-d-吡喃葡萄糖基）-d-半乳糖-1,4-内酯（7）是通过将6-O-三苯甲基-2,3,5-三-O-苯甲酰基-d-半乳糖-1,4-内酯（2）与2,3,4,6-四-O缩合而制得-乙酰基-α-d-吡喃葡萄糖基溴化物（4）或与1,2,3,4,6-戊-O-乙酰基-β-d-吡喃葡萄糖（6）。使用各种催化剂进行反应。在三氟甲磺酸银或氯化锡（IV）的存在下，立体选择性地形成1,2-反式糖苷键，以高收率得到化合物7。然而，由汞盐催化的2,3,5-三-O-苯甲酰基-d-半内酯-1,4-内酯（3）与4的缩合得到3,4,6-三-O-乙酰基-1,2 -O-[1（S）-（2,3,5-三-O-苯甲酰基-d-半乳糖基-1，以4-内酯-6-烷氧基）亚乙基]-α-d-吡喃葡萄糖（5）为主要产物。用双（3-甲基-2-丁基）硼烷还原7的内酯功能导致2

  DOI：

  10.1016/0008-6215(89)84087-x
• 作为产物：
  描述：

  D-半乳糖酸-1,4-内酯 在 吡啶 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 2,3,5-tri-O-benzoyl-D-galactono-1,4-lactone
  参考文献：
  名称：

  一种以呋喃糖为还原单元的二糖衍生物合成的新方法

  摘要：

  摘要内酯二糖2,3,5-三-O-苯甲酰基-6-O-（2,3,4,6-四-O-乙酰基-β-d-吡喃葡萄糖基）-d-半乳糖-1,4-内酯（7）是通过将6-O-三苯甲基-2,3,5-三-O-苯甲酰基-d-半乳糖-1,4-内酯（2）与2,3,4,6-四-O缩合而制得-乙酰基-α-d-吡喃葡萄糖基溴化物（4）或与1,2,3,4,6-戊-O-乙酰基-β-d-吡喃葡萄糖（6）。使用各种催化剂进行反应。在三氟甲磺酸银或氯化锡（IV）的存在下，立体选择性地形成1,2-反式糖苷键，以高收率得到化合物7。然而，由汞盐催化的2,3,5-三-O-苯甲酰基-d-半内酯-1,4-内酯（3）与4的缩合得到3,4,6-三-O-乙酰基-1,2 -O-[1（S）-（2,3,5-三-O-苯甲酰基-d-半乳糖基-1，以4-内酯-6-烷氧基）亚乙基]-α-d-吡喃葡萄糖（5）为主要产物。用双（3-甲基-2-丁基）硼烷还原7的内酯功能导致2

  DOI：

  10.1016/0008-6215(89)84087-x

文献信息

• Synthesis of galactofuranose disaccharides of biological significance
  作者：Carla Marino、Oscar Varela、Rosa M. de Lederkremer

  DOI：10.1016/0008-6215(89)84147-3

  日期：1989.7

  disaccharide derivative having both units in the furanoid form. Thus, diisoamylborane reduction of the lactone function of 6 led to the disaccharide derivative 10, from which the methyl glycoside 12 was prepared. O-Debenzoylation of 12 gave the corresponding methyl beta-D-galactofuranosyl-(1----6)-beta-D-galactofuranoside. The free disaccharide beta-D-Galf-(1----6)-D-Galp and its acetylated derivative were

  通过氯化锡（IV）催化五-O-苯甲酰基-α，β-D-半乳糖呋喃糖的糖基化，然后用甲醇钠进行脱苯甲酰化，可以轻松获得甲基β-D-半乳糖呋喃糖苷。将1，与2,3,5-三-O-苯甲酰基-D-半乳糖基-1,4-内酯或与6-O-三苯甲基-内酯衍生物5进行糖基化，得到苯甲酰化的β-D-D-半呋喃糖基-（1- --6）-D-半乳糖-1,4-内酯6，收率极高。通过硼氢化物还原成糖基-糖醇7证实了二糖6的结构。1与4或5的缩合反应的副产物被鉴定为苯甲酰化的（1-1）-β，β'-D-半乳糖呋喃糖基二糖8。在氯化锡的存在下，通过向1中加水可容易地制备化合物8（收率88％）。8的O-脱苯甲酰化得到结晶的β' -D-半呋喃糖基-（1 ---- 1）-β-D-半呋喃糖苷 糖基内酯6构成用于合成具有两个呋喃形式的二糖衍生物的关键中间体。因此，内酯官能团的二异戊基硼烷还原导致二糖衍生物10，由此制备了甲基糖苷12。12的
• Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan
  作者：Lucía Gandolfi-Donadío、Carola Gallo-Rodriguez、Rosa M. de Lederkremer

  DOI：10.1016/j.carres.2008.01.024

  日期：2008.7

  conveniently derivatized for further elongation. The strategy relied on the use of suitably substituted D-galactono-1,4-lactones as precursors for the galactofuranose units. Reduction of lactone tetrasaccharide 9 with disiamylborane afforded the tetrasaccharide synthon 1. The tetrasaccharide contains the linker unit of the arabinan to the galactan.

  分枝杆菌的阿拉伯半乳聚糖含有呋喃糖环形式的两种单糖，在哺乳动物中不存在。我们在这里报告四糖片段α-D-Araf-（1-> 5）-beta-D-Galf-（1-> 5）-beta-D-Galf-（1-> 6的首次合成）-D-Galf，可方便地衍生化以进一步延长。该策略依赖于使用适当取代的D-半乳糖-1,4-内酯作为半乳糖呋喃糖单元的前体。用二戊基硼烷还原内酯四糖9得到四糖合成子1。四糖含有阿拉伯聚糖与半乳聚糖的连接单元。
• Facile Synthesis of per-<i>O-tert</i>-Butyldimethylsilyl-β-<scp>d</scp>-galactofuranose and Efficient Glycosylation via the Galactofuranosyl Iodide
  作者：Luciana Baldoni、Carla Marino

  DOI：10.1021/jo8025274

  日期：2009.3.6

  The synthesis of crystalline per-O-TBS-beta-D-galactofuranose (4 beta) as a new precursor of D-Galf units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly Of D-galactofuranosyl moieties with high beta-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved.
• Syntheses of β-<scp>d</scp>-Gal<i>f</i>-(1→6)-β-<scp>d</scp>-Gal<i>f</i>-(1→5)-<scp>d</scp>-Gal<i>f</i> and β-<scp>d</scp>-Gal<i>f</i>-(1→5)-β-<scp>d</scp>-Gal<i>f</i>-(1→6)-<scp>d</scp>-Gal<i>f</i>, Trisaccharide Units in the Galactan of <i>Mycobacterium </i><i>t</i><i>uberculosis</i>
  作者：Lucía Gandolfi-Donadío、Carola Gallo-Rodriguez、Rosa M. de Lederkremer

  DOI：10.1021/jo034365o

  日期：2003.9.1

  The galactofuran is a crucial constituent of the cell wall of mycobacteria. An efficient synthesis of the two trisaccharide units of the galactan is described. The strategy relies on the use of substituted D-galactono-1,4-lactones as precursors for the internal and the reducing galactofuranoses. Dec-9-enyl beta-D-Galf-(1-->6)-beta-D-Galf-(1-->5)-beta-D-Galf (2) and dec-9-enyl beta-D-Galf-(1-->5)-beta-D-Galf-(1beta6)-beta-D-Galf (9) so far reported as convenient substrates for the galactofaranosyl transferase, and possibly useful for immunological studies, were obtained by the trichloroacetimidate method of glycosylation.
• Glycosylation studies on conformationally restricted 3,5-O-(di-tert-butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation
  作者：Mariano J. Tilve、Carola Gallo-Rodriguez

  DOI：10.1016/j.carres.2011.10.004

  日期：2011.10

  Conformationally restricted 3,5-O-di-tert-butylsilylene-D-galactofuranosyl trichloroacetimidate donors were synthesized from allyl alpha-D-galactofuranoside for the construction of 1,2-cis alpha-D-galactofuranosyl linkages. Glycosylation reactions were performed with several acceptors, including D-galactono-1,4-lactone, D-rhamnopyranosyl, and D-mannopyranosyl derivatives. The influence of the temperature and the reaction solvents was evaluated, as well as the 6-O-substitution pattern of the donor. The higher alpha-selectivities were obtained at -78 degrees C in diethyl ether as solvent. 6-O-Acetyl substitution on constrained donor increased the alpha-selectivity compared to the 6-O-benzyl substitution. Almost no selectivities were observed in the non-participating solvent CH2Cl2. In contrast, ethereal solvents enhanced the alpha-selectivity suggesting a participating effect in the reaction intermediate. (C) 2011 Elsevier Ltd. All rights reserved.