2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate | 251451-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate
• 英文别名: O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl) trichloroacetimidate；2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl trichloroacetamidate；2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl trichloroacetimidate；Perbenzoylated arabinofuranosyl trichloroacetimidate；[(2S,3S,4R,5S)-3,4-dibenzoyloxy-5-(2,2,2-trichloroethanimidoyl)oxyoxolan-2-yl]methyl benzoate
• CAS: 251451-05-5
• 化学式: C₂₈H₂₂Cl₃NO₈
• 分子量: 606.844
• InChiKey: SXPAELVWHIZWAY-IFOBJOEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [(2S,3S,4R,5S)-5-[[(3aR,5S,6S,6aR)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  A simple approach to 3,6-branched galacto-oligosaccharides and its application to the syntheses of a tetrasaccharide and a hexasaccharide related to the arabinogalactans (AGs)

  摘要：

  The preparation of 1,2:5,6-di-O-isopropylidene-alpha-D-galactofuranose was improved by increasing the ratio of DMF to acetone and using a solid supported catalyst. Employing the easily accessible 1, 2:5,6-di-O-isopropylidene-alpha-D-galactofuranose as the starting glycosyl acceptor, a method which is particularly suitable for the regio- and stereoselective syntheses of 3,6-branched galacto-oligosaccharides was developed. A tetrasaccharide and a hexasaccharide related to the arabinogalactans (AGs) from plants were readily prepared using this strategy. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01717-3
• 作为产物：
  描述：

  L-lyxose 在 吡啶 、 potassium carbonate 、 乙酰氯 、 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate
  参考文献：
  名称：

  糖基化Genipin衍生物作为新型抗病毒剂，杀虫剂和杀真菌剂的发现。

  摘要：

  设计并合成了一系列新颖的Genipin糖苷衍生物，该衍生物在Genipin的1或10位上包含11个糖苷部分。这些化合物显示出对烟草花叶病毒的中等至优异的抑制活性。特别地，化合物6e，7c，7d，7f，7h和7i的体外和体内活性与利巴韦林相当。特别是化合物7c，Genipin的甘露糖基衍生物在10位上，表现出最好的活性。该系列的京尼平糖基衍生物还显示出对14种植物致病真菌的杀真菌活性，特别是对谷物弹状根病菌和核盘菌（Sclerotiania sclerotiorum）。而且，化合物6h对小菜蛾显示出良好的杀虫活性。化合物7b，7c和7g对三种鳞翅目害虫（东方粘虫，棉铃虫和玉米bore）表现出中等的杀虫活性。化合物7e表现出优异的杀灭蚊子的幼虫活性。

  DOI：

  10.1021/acs.jafc.7b05861

文献信息

• Synthesis of furostanol glycosides: discovery of a potent α-glucosidase inhibitor
  作者：Peng Wang、Jiejie Hao、Xiuli Zhang、Cong Wang、Huashi Guan、Ming Li

  DOI：10.1039/c6ob01766e

  日期：——

  A convenient approach to the synthesis of furostanol glycosides has been developed with the features of both highly efficient incorporation of a 26-O-β-D-glucopyranosyl unit and ready formation of hemiketal ring E. The total syntheses of seven furostanol saponins including funlioside B, lilioglycoside, protobioside I, protodioscin, pallidifloside I, coreajaponins A and parisaponin I are efficiently

  已经开发了一种方便的合成糠醛甾醇糖苷的方法，该方法具有高效掺入26- O- β- D-吡喃葡萄糖基单元和易于形成半缩酮环E的特点。七种糠醛甾醇皂苷的总合成包括fun素B使用容易获得的16β-乙酰氧基-22-氧代-26-羟基胆甾醇衍生物作为有效的构建基块可有效地获得，，，，，、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、还评估了合成皂苷的α-葡萄糖苷酶抑制活性，这表明fun药苷B是开发α-葡萄糖苷酶抑制剂的高度潜在的先导。
• Synthesis of oligosaccharide derivatives related to those from sanqi, a Chinese herbal medicine from Panax notoginseng
  作者：Feng Yang、Yuguo Du

  DOI：10.1016/s0008-6215(02)00013-7

  日期：2002.3

  nosyl-(1-->4)-beta-D-galactopyranosyl-(1-->3)-[alpha-L-arabinofuranosyl-(1-->6)]-alpha-D-galactopyranoside, were synthesized under standard glycosylation conditions. An unexpected alpha-(1-->4) linkage was formed predominantly in the presence of neighboring participation group during regioselective synthesis of hexasaccharide via 3+3 strategy.

  来自三七的中草药三七的寡糖衍生物，甲基β-D-吡喃半乳糖基-（1-> 3）-[α-L-阿拉伯呋喃糖基-（1-> 6）]-α-D-吡喃半乳糖苷，薯os基β-D-吡喃半乳糖基-（1-> 3）-[α-L-阿拉伯呋喃糖基-（1→6）]-α-D-吡喃半乳糖苷和甲基β-D-吡喃半乳糖基-（1- > 3）-[α-L-阿拉伯呋喃糖基-（1-> 6）]-α-D-吡喃半乳糖基-（1-> 4）-β-D-吡喃半乳糖基-（1-> 3）-[α在标准糖基化条件下合成了-L-阿拉伯呋喃糖基-（（1→6）]-α-D-吡喃半乳糖苷。通过3 + 3策略在区域选择性合成六糖的过程中，在相邻的参与基团的存在下主要形成了意想不到的alpha-（1-4）连接。
• An Efficient Method for the Synthesis of 2,6-Branched Galacto-Oligo­saccharides and Its Applications to the Synthesis of Three Tetrasaccharides and a Hexasaccharide Related to the Arabinogalactans (AGs)
  作者：Jun Ning、Yuetao Yi、Zhe Yao

  DOI：10.1055/s-2003-42109

  日期：——

  An efficient method for the synthesis of 2,6-branched galacto-oligosaccharides has been developed by using 6-O-Ac-2,3,4-tri-O-Bz-α-d-galactopyranosyl trichloroacetimidate, 2,6-di-O-Ac-3,4-di-O-Bz-α-d-galactopyranosyl trichloroacetimidate and 2-O-Ac-3,4,6-tri-O-Bz-α-d-galactopyranosyl trichloroacetimidate as synthons. Three tetrasaccharides and a hexasaccharides related to AGs from plants were readily prepared using this method.

  通过使用6-O-Ac-2,3,4-三-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺、2,6-二-O-Ac-3,4-二-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺和2-O-Ac-3,4,6-三-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺作为合成砌块，开发了一种高效合成2,6-支化半乳寡糖的方法。利用这种方法，可以方便地制备与植物来源的AGs相关的三种四糖和一种六糖。
• Synthesis of a hexasaccharide that relates to the arabinogalactan epitope
  作者：Guofeng Gu、Feng Yang、Yuguo Du、Fanzuo Kong

  DOI：10.1016/s0008-6215(01)00259-2

  日期：2001.11

  A hexasaccharide derivative of the arabinogalactan epitope, methyl beta-D-galactopyranosyl-(1-->6)-[alpha-L-arabinofuranosyl-(1-->3)]-beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranosyl-(1-->6)-[alpha-L-arabinofuranosyl-(1-->3)]-alpha-D-galactopyranoside, was synthesized efficiently using a 3+3 strategy. The key step is the preparation of the trisaccharide donor, isopropyl 2,3,4,6-tetra-O-benz

  阿拉伯半乳糖抗原决定簇的六糖衍生物，甲基β-D-吡喃半乳糖基-（1-> 6）-[α-L-阿拉伯呋喃糖基-（1-> 3）]-β-D-吡喃半乳糖基-（1-> 6）-β-D-吡喃半乳糖基-（1→6）-[α-L-阿拉伯呋喃糖基-（1→3）]-α-D-吡喃半乳糖苷是使用3 + 3策略有效合成的。关键步骤是制备三糖供体异丙基2,3,4,6-四-O-苯甲酰基-β-D-吡喃半乳糖基-（1-> 6）-[2,3,5-tri-O -异丙基1-硫代-β-D-吡喃半乳糖苷中的-苯甲酰基-α-L-阿拉伯呋喃糖基-（（1-> 3）]-2,4-二-O-苯甲酰基-1-硫代-β-D-吡喃半乳糖苷一锅合成3,6-差异保护的构建基块。
• Regio- and Stereoselective Synthesis of 1 → 5-Linked α-l-Arabinofuranosyl Oligosaccharides
  作者：Yuguo Du、Qingfeng Pan、Fanzuo Kong

  DOI：10.1055/s-1999-3170

  日期：——

  Regio- and stereoselective synthesis of furanosyl oligosaccharides in moderate to very good yields using arabinofuranosyl trichloroacetimidates as glycosyl donors and unprotected or partially protected glycosides as acceptors was described. A convergent synthesis of 1 → 5-linked α-l-arabinofuranosyl octamer was presented.

  以阿拉伯呋喃糖基三氯乙酰亚氨酸酯为糖基供体，以未保护或部分保护的糖苷为受体，描述了呋喃糖基寡糖的区域和立体选择性合成，产率中等至非常好。介绍了 1 → 5 连接的δ-±-阿拉伯呋喃糖基八聚体的聚合合成。