3-methyl-2-butenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside | 1221234-31-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-methyl-2-butenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside
• 英文别名: (2S,4aR,6R,7R,8R,8aR)-6-(3-methylbut-2-enoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 1221234-31-6
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: YCJNOXUAGVYWMC-BLONOQDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3-methyl-2-butenyl 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87%的产率得到3-methyl-2,3-[N-(4-methylbenzenesulfonyl)imino]butyl 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：

  prenyl β-D-galactopyranoside 、 苯甲醛二甲缩醛 在 camphor-10-sulfonic acid 、 三乙胺 作用下， 以 乙腈 为溶剂， 以86%的产率得到3-methyl-2-butenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Alkenyl β-d-galactopyranoside derivatives as efficient chiral templates in stereoselective cyclopropanation and epoxidation reactions

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2009.12.003

文献信息

• 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.
• 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.