2-methyl-2-propenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside | 1221234-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-methyl-2-propenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside
• 英文别名: (2S,4aR,6R,7R,8R,8aR)-6-(2-methylprop-2-enoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 1221234-32-7
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: SBLHKDLUIAJRRN-ZBURPKILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methyl-2-propenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 、 chloramine T trihydrate 在 phenyltrimethylammonium tribromide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以65%的产率得到2-methyl-2,3-[N-(4-methylbenzenesulfonyl)imino]propyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Aziridines from alkenyl-β-D-galactopyranoside derivatives: Stereoselective synthesis and in vitro selective anticancer activity

  摘要：

  A series of new aziridines beta-D-galactopyranoside derivatives were synthesized from alkenyl beta-D-galactopyranosides employing Sharpless conditions. The structures of the compounds were established by H-1 NMR, C-13 NMR, MS, HRMS and elemental analysis. The stereoselectivity of the reaction and the structural requirements of the alkenyl precursor for improving diastereoisomeric excesses of the direct aziridination reaction were also studied.The new compounds were subjected to a preliminary screening for cytotoxic activity against human lung cancer cells vs. human non-malignant lung cells. Terminal aziridine derivatives showed activity and, most notably, selectivity. One of the most active and selective compounds was also evaluated against breast cancer cells, melanoma cells, and non-malignant cells from the same origin. Its cytotoxic activity was similar to that of the positive controls, displaying a highly selective cytotoxic activity against both types of cancer cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.020
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 camphor-10-sulfonic acid 、 sodium methylate 、 mercury(II) cyanide 作用下， 以 甲醇 、 硝基甲烷 、 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成 2-methyl-2-propenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  烯基 β-D-Hexopyranosides 的立体选择性二羟基化反应：合成糖基甘油衍生物和 1-O-Acyl-3-O-β-D-糖基-sn-甘油类似物的方法

  摘要：

  在 Donohoe 条件下，通过一系列烯基 β-D-己酮苷的立体选择性二羟基化，制备了多种新的糖基甘油衍生物。我们研究了非对映异构体过量与前体（糖和烯基部分）的结构特征之间的关系。立体化学产率表明糖部分的 2 位存在氢键供体基团 (OH, NHAc) 是获得高水平立体识别力所必需的。新的 1-O-酰基-3-O-β-D-糖基-sn-甘油类似物是通过用脂肪酸对伯羟基进行官能化而获得的。还提供了糖基甘油和糖基甘油脂类似物的初步细胞毒活性分析。

  DOI：

  10.1002/ejoc.201101539

文献信息

• Alkenyl β-d-galactopyranoside derivatives as efficient chiral templates in stereoselective cyclopropanation and epoxidation reactions
  作者：José M. Vega-Pérez、Ignacio Periñán、Carlos Palo-Nieto、Margarita Vega-Holm、Fernando Iglesias-Guerra

  DOI：10.1016/j.tetasy.2009.12.003

  日期：2010.1

  The synthesis of a wide range of alkenyl 4,6-O-(S)-benzylidene-beta-D-galactopyranosides is described. The cyclopropanation and epoxidation reactions of these compounds were developed. Cyclopropanation reactions took place with high stereoselectivity giving diastereomeric excesses of up to 100%. As a part Of Our aim in studying hydroxyl-directed reactions, their epoxidation with m-CPBA was carried out High diastereomeric excesses (80-100%) were obtained when the hydroxyl group at C-2 of the auxiliary was unprotected The beta-D-galactopyranoside moiety constitutes as an interesting auxiliary, due to its efficient chirality transfer capability as well as providing a way to obtain a variety of glycolipid derivatives (c) 2009 Elsevier Ltd All rights reserved.
• Aziridines from alkenyl-β-D-galactopyranoside derivatives: Stereoselective synthesis and in vitro selective anticancer activity
  作者：José M. Vega-Pérez、Carlos Palo-Nieto、Margarita Vega-Holm、Purificación Góngora-Vargas、José Manuel Calderón-Montaño、Estefanía Burgos-Morón、Miguel López-Lázaro、Fernando Iglesias-Guerra

  DOI：10.1016/j.ejmech.2013.10.020

  日期：2013.12

  A series of new aziridines beta-D-galactopyranoside derivatives were synthesized from alkenyl beta-D-galactopyranosides employing Sharpless conditions. The structures of the compounds were established by H-1 NMR, C-13 NMR, MS, HRMS and elemental analysis. The stereoselectivity of the reaction and the structural requirements of the alkenyl precursor for improving diastereoisomeric excesses of the direct aziridination reaction were also studied.The new compounds were subjected to a preliminary screening for cytotoxic activity against human lung cancer cells vs. human non-malignant lung cells. Terminal aziridine derivatives showed activity and, most notably, selectivity. One of the most active and selective compounds was also evaluated against breast cancer cells, melanoma cells, and non-malignant cells from the same origin. Its cytotoxic activity was similar to that of the positive controls, displaying a highly selective cytotoxic activity against both types of cancer cells. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Stereoselective Dihydroxylation Reaction of Alkenyl β-D-Hexopyranosides: A Methodology for the Synthesis of Glycosylglycerol Derivatives and 1-O-Acyl-3-O-β-D-glycosyl-sn-glycerol Analogues
  作者：José M. Vega-Pérez、Carlos Palo-Nieto、Ignacio Periñán、Margarita Vega-Holm、José M. Calderón-Montaño、Miguel López-Lázaro、Fernando Iglesias-Guerra

  DOI：10.1002/ejoc.201101539

  日期：2012.2

  A variety of new glycosylglycerol derivatives have been prepared by stereoselective dihydroxylation of a range of alkenyl β-D-hexopyanosides under Donohoe's conditions. We have studied the relationship between the diastereoisomeric excess and the structural features of the precursor (sugar and alkenyl moieties). The stereochemical yields demonstrated that the presence of a hydrogen-bond donor group

  在 Donohoe 条件下，通过一系列烯基 β-D-己酮苷的立体选择性二羟基化，制备了多种新的糖基甘油衍生物。我们研究了非对映异构体过量与前体（糖和烯基部分）的结构特征之间的关系。立体化学产率表明糖部分的 2 位存在氢键供体基团 (OH, NHAc) 是获得高水平立体识别力所必需的。新的 1-O-酰基-3-O-β-D-糖基-sn-甘油类似物是通过用脂肪酸对伯羟基进行官能化而获得的。还提供了糖基甘油和糖基甘油脂类似物的初步细胞毒活性分析。