2,3,4-tri-O-benzyl-β-L-rhamnopyranose 1-O-trichloroacetimidate | 103368-09-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-β-L-rhamnopyranose 1-O-trichloroacetimidate
• 英文别名: [(2R,3R,4R,5S,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl] 2,2,2-trichloroethanimidate
• CAS: 103368-09-8
• 化学式: C₂₉H₃₀Cl₃NO₅
• 分子量: 578.92
• InChiKey: UKYLUZBNQWVCNG-CMKGNXEASA-N

物化性质

• 沸点：
  598.7±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.85
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  70.0
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-β-L-rhamnopyranose 1-O-trichloroacetimidate 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， -10.0~25.0 ℃ 、101.33 kPa 条件下， 反应 1.67h， 生成 伊夫单甙
  参考文献：
  名称：

  Cardiac glycosides. 7. Sugar stereochemistry and cardiac glycoside activity

  摘要：

  Digitoxigenin alpha-L-, beta-L-, alpha-D-, and beta-D-glucosides; alpha-L-, beta-L-, alpha-D-, and beta-D-mannosides; and alpha-L- and beta-L-rhamnosides were stereoselectively synthesized from the corresponding sugar tetrabenzyl trichloroacetimidates. The Na+,K+-ATPase receptor inhibitory activities of these glycosides (as a measure of receptor binding) were compared with those of digitoxigenin, digitoxigenin 6'-hydroxy-beta-D-digitoxoside, digitoxigenin beta-D-galactoside, and digitoxigenin beta-D-digitoxoside. The observed activities reveal that a given sugar substituent may have a role in binding of some glycoside stereoisomers, but not others. With alpha-L- and possibly beta-L-rhamnosides, the 5'-CH3 and 4'-OH appear to have a predominant role in binding to the Na+,K+-ATPase receptor. Addition of a 6'-OH to form the corresponding mannosides dramatically disrupts the effect of both the 5'-CH3 and 4'-OH in prompting receptor binding of the alpha-L isomer. However, with the beta-L isomer, some influence of 4'-OH, 3'-OH, and 2'-OH binding remains. With beta-D-glycosides, binding via the "5'-CH3 site" appears to be of little importance and addition of a 6'-OH diminishes activity only slightly. With these beta-D-glycosides, an equatorial 4'-OH, axial 3'-OH, and equatorial 2'-OH groups appear to contribute to binding.

  DOI：

  10.1021/jm00160a025
• 作为产物：
  描述：

  甲基-Alpha-D-吡喃鼠李糖苷 在 盐酸 、 氢氧化钾 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.33h， 生成 2,3,4-tri-O-benzyl-β-L-rhamnopyranose 1-O-trichloroacetimidate
  参考文献：
  名称：

  Cardiac glycosides. 7. Sugar stereochemistry and cardiac glycoside activity

  摘要：

  Digitoxigenin alpha-L-, beta-L-, alpha-D-, and beta-D-glucosides; alpha-L-, beta-L-, alpha-D-, and beta-D-mannosides; and alpha-L- and beta-L-rhamnosides were stereoselectively synthesized from the corresponding sugar tetrabenzyl trichloroacetimidates. The Na+,K+-ATPase receptor inhibitory activities of these glycosides (as a measure of receptor binding) were compared with those of digitoxigenin, digitoxigenin 6'-hydroxy-beta-D-digitoxoside, digitoxigenin beta-D-galactoside, and digitoxigenin beta-D-digitoxoside. The observed activities reveal that a given sugar substituent may have a role in binding of some glycoside stereoisomers, but not others. With alpha-L- and possibly beta-L-rhamnosides, the 5'-CH3 and 4'-OH appear to have a predominant role in binding to the Na+,K+-ATPase receptor. Addition of a 6'-OH to form the corresponding mannosides dramatically disrupts the effect of both the 5'-CH3 and 4'-OH in prompting receptor binding of the alpha-L isomer. However, with the beta-L isomer, some influence of 4'-OH, 3'-OH, and 2'-OH binding remains. With beta-D-glycosides, binding via the "5'-CH3 site" appears to be of little importance and addition of a 6'-OH diminishes activity only slightly. With these beta-D-glycosides, an equatorial 4'-OH, axial 3'-OH, and equatorial 2'-OH groups appear to contribute to binding.

  DOI：

  10.1021/jm00160a025

文献信息

• 一种1,5-烯炔醇类化合物及其合成方法和应用
  申请人：陕西师范大学

  公开号：CN104513137B

  公开（公告）日：2016-05-04

  本发明公开了一种1,5-烯炔醇类化合物及其合成方法和应用，该化合物的结构式为式中R1代表烷基或芳基，R代表卤素、烷基、烷氧基、硝基或酯基，w为0～2的任意整数。本发明的1,5-烯炔醇类化合物可通过Fishcher成苷法、Schmidt成苷法引入糖端基成为糖基供体的醚类离去基团，该基团可在催化量Au(Ⅰ)活化下关环离去，使糖基供体与受体发生偶联反应进而构建糖苷键；同时该化合物可直接引至糖端位作为糖端位保护基，该保护基对酸性条件、碱性条件具有一定的耐受性，并且具有一定的耐高温性质，在糖模块保护及去保护的合成操作过程中具有良好的稳定性，可简化糖模块的合成步骤。
• Visible-light-induced photoacid catalysis: application in glycosylation with <i>O</i>-glycosyl trichloroacetimidates
  作者：Gaoyuan Zhao、Juncheng Li、Ting Wang

  DOI：10.1039/d1cc04887b

  日期：——

  The development of visible-light-induced photoacid catalyzed glycosylation is reported.

  可见光诱导的光酸催化糖基化反应的发展被报道。