2,3,4-三-O-乙酰基-β-D-吡喃木糖基三氯乙酰亚胺酸酯 | 128377-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,3,4-三-O-乙酰基-β-D-吡喃木糖基三氯乙酰亚胺酸酯
• 英文名称: 2,3,4-tri-O-acetyl-β-D-xylopyranosyl trichloroacetimidate
• 英文别名: 2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl trichloroacetimidate；[(3R,4S,5R,6S)-4,5-diacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate
• CAS: 128377-34-4
• 化学式: C₁₃H₁₆Cl₃NO₈
• 分子量: 420.631
• InChiKey: NAGHJYXWJQCCPK-YTWAJWBKSA-N

物化性质

• 沸点：
  395.3±52.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4-三-O-乙酰基-β-D-吡喃木糖基三氯乙酰亚胺酸酯 在 4 A molecular sieve 、 三氟化硼乙醚 、 乙酸肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 Acetic acid (2R,3R,4S,5R)-5-acetoxy-2-acetoxymethyl-6-hydroxy-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of three diosgenyl saponins: dioscin, polyphyllin D, and balanitin 7

  摘要：

  Dioscin, polyphyllin D, and balanitin 7, which belong to a group of structurally similar diosgenyl saponins with promising bioactivities, were synthesized by stepwise glycosylation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00066-x
• 作为产物：
  描述：

  1,2,3,4-四-O-乙酰基吡喃戊糖 在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 2,3,4-三-O-乙酰基-β-D-吡喃木糖基三氯乙酰亚胺酸酯
  参考文献：
  名称：

  软体动物系列糖基神经酰胺α-d-Manp-（1→3）-β-d-Manp-（1→4）-β-d-Glcp-（1→1）-Cer和α-d的全合成-Manp-（1→3）-[β-d-Xylp-（1→2）]-β-d-Manp-（1→4）-β-d-Glcp-（1→1）-Cer

  摘要：

  摘要软体动物系列糖鞘脂，O-α-d-甘露吡喃糖基-（1→3）-O-β-d-甘露吡喃糖基-（1→4）-O-β-d-吡喃葡萄糖基-（1→1）-2 -N-十四烷酰基-（4E）-鞘氨醇和O-α-d-甘露吡喃糖基-（1→3）-O- [β-d-吡喃吡喃糖基-（1→2）]-O-β-d-甘露吡喃糖基-（利用2,3,4-三-O-乙酰基首次合成了1→4）-O-β-d-吡喃葡萄糖基-（1→1）-2-N-十四烷酰基-（4E）-鞘氨醇-d-木吡喃糖基三氯乙酰亚胺酸酯，甲基2,3,4,6-四-O-乙酰基-1-硫代-α-d-甘露吡喃糖苷，苄基O-（4,6-二-O-苄基-β-d-甘露吡喃糖基）-（1→4）-2,3,6-三-O-苄基-β-d-吡喃葡萄糖苷9和（2S，3R，4E）-2-叠氮基-3-O-（叔丁基二苯基甲硅烷基）-以4-十八碳烯-1,3-二醇6为主要中间体。六-O-苄基二糖9是通过偶联两个2,3-二-O-烯丙基-

  DOI：

  10.1016/0008-6215(90)84167-s

文献信息

• Chemical synthesis of the pentasaccharide related to the anti-inflammatory oleanane type saponins isolated from medicinal plant Aster tataricus L. f.
  作者：Madhumita Bera、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2022.108563

  日期：2022.6

  Total synthesis of the pentasaccharide related to the saponin isolated from the medicinal plant Aster tataricus L. f. is reported in the form of its allyl glycoside. The synthesis is accomplished by following a [3 + 2] block synthesis strategy where the trisaccharide acceptor and the disaccharide donor are rationally designed and obtained from semi-protected monosaccharides through stereoselective

  从药用植物Aster tataricus L. f.中分离的皂苷相关五糖的全合成 以其烯丙基糖苷的形式报道。该合成是通过遵循 [3 + 2] 嵌段合成策略完成的，其中三糖受体和二糖供体经过合理设计，并通过立体选择性糖基化从半保护的单糖中获得，或者通过激活硫糖苷或糖基三氯乙酰亚胺酯。apiose 部分已通过文献程序合成，几乎没有修改。其烯丙基糖苷形式的目标五糖将有利于进一步生物学评价所述结构和根据需要可能形成的糖缀合物。
• Novel compounds
  申请人：——

  公开号：US20030092637A1

  公开（公告）日：2003-05-15

  The present invention relates to combinations of xylose compounds with other pharmaceutically active compounds, to pharmaceutical compositions comprising said combinations, as well as to use of these combinations for the manufacture of a medicament for treatment of proliferative disorders. In another aspect, the present invention relates to novel xylose compounds, to pharmaceutical compositions comprising said compounds, and to use of these compounds for the manufacture of a medicament or the treatment of proliferative disorders.

  本发明涉及木糖化合物与其他药用活性化合物的组合物、包含所述组合物的药物组合物，以及使用这些组合物制造治疗增殖性疾病的药物。另一方面，本发明涉及新型木糖化合物、包含上述化合物的药物组合物，以及使用这些化合物制造药物或治疗增殖性疾病。
• Effects of oxygen–sulfur substitution on glycosaminoglycan-priming naphthoxylosides
  作者：Mårten Jacobsson、Katrin Mani、Ulf Ellervik

  DOI：10.1016/j.bmc.2007.05.008

  日期：2007.8

  Three series of sulfur-containing analogs to the selectively antiproliferative 2-(6-hydroxynaphthyl) beta-D-xylopyranoside were synthesized and their biological properties investigated. A short, general route to hydroxynaphthyl disulfides from dihydroxy-naphthalenes was developed to utilize the disulfide bond as a sulfur-selective protecting group to enable the orthogonal protection of hydroxyls and thiols. The results indicate that hydrophobic, uncharged oxygen-sulfur substituted naphthoxylosides are taken up by calls and initiate priming of GAG chains to a greater extent compared to the oxygen analogs. No correlation between priming ability and antiproliferative activity was observed. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and anti-nociceptive and anti-inflammatory effects of gaultherin and its analogs
  作者：Chao Wang、Tian-Tai Zhang、Guan-Hua Du、Dong-Ming Zhang

  DOI：10.1080/10286020.2011.596830

  日期：2011.9

  The synthesis of gaultherin (1) and its analogs was carried out to provide 11 glycosides under phase-transfer catalytic conditions. The activities of all synthesized compounds were evaluated by nitric oxide production inhibitory assay in vitro. Methyl 2-O-(4-O-beta-D-galactopyranosyl)-beta-D-glucopyranosylbenzoate (5f) showed significantly antinociceptive and anti-inflammatory effects by the evaluation in vivo. Structure-activity relationships within these compounds were discussed.
• Synthesis of a Series of Monosaccharide–Fipronil Conjugates and Their Phloem Mobility
  作者：Jian-Guo Yuan、Han-Xiang Wu、Meng-Ling Lu、Gao-Peng Song、Han-Hong Xu

  DOI：10.1021/jf400888c

  日期：2013.5.8

  To test the effect of adding different monosaccharide groups to a non-phloem-mobile insecticide on the phloem mobility of the insecticide, a series of conjugates of different monosaccharides and fipronil were synthesized using the trichloroacetimidate method. Phloem mobility tests in castor bean (Ricinus communis L.) seedlings indicated that the phloem mobility of these conjugates varied markedly. L-Rhamnose fipronil and D-fucose fipronil displayed the highest phloem mobility among all of the tested conjugates. Conjugating hexose, pentose, or deoxysugar to fipronil through an O-glycosidic linkage can confer phloem mobility to fipronil in R. communis L. effectively, while the -OH orientation of the monosaccharide substantially affected the phloem mobility of the conjugates.