1-O-hexadecyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-sn-glycerol | 459432-40-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-O-hexadecyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-sn-glycerol
• 英文别名: (2R)-1-hexadecoxy-3-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropan-2-ol
• CAS: 459432-40-7
• 化学式: C₅₃H₇₄O₈
• 分子量: 839.166
• InChiKey: WZLQIRFIKOMGDO-HCBCKETRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  61
• 可旋转键数：
  33
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-O-hexadecyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-sn-glycerol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 1-O-hexadecyl-2-O-palmitoyl-3-O-(β-D-galactopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis of galactoglycerolipids found in the HT29 human colon carcinoma cell line

  摘要：

  Synthesis of three galactoglycerolipids (3-O-(beta-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl)-1-O-hexadecyl-sn-glycerol), and the corresponding glycerolipid (1-O-hexadecyl-2-O-palmitoyl-sn-glycerol) is described. The first two compounds were recently identified in the human colon carcinoma cell line HT29. The three-carbon synthon (S)-glycidol was used for construction of the glycerol moiety. Glycosylation of (S)-glycidol with protected galactosyl and digalactosyl donors produced galactosyl and digalactosyl glycidols. Lewis acid catalyzed opening of the epoxide produced protected galactosyl and digalactosyl glycerolipids. Deprotection, or palmitoylation followed by deprotection, yielded the target compounds. The corresponding glycerolipid was synthesized analogously and an oxidation-reduction procedure for tritiation was developed. The synthesized compounds will be used in studies of the role of galactosyl glycerolipids in differentiation and colon cancer development. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00473-8
• 作为产物：
  描述：

  (R)-glycidyl-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside 在 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1-O-hexadecyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis of galactoglycerolipids found in the HT29 human colon carcinoma cell line

  摘要：

  Synthesis of three galactoglycerolipids (3-O-(beta-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl)-1-O-hexadecyl-sn-glycerol), and the corresponding glycerolipid (1-O-hexadecyl-2-O-palmitoyl-sn-glycerol) is described. The first two compounds were recently identified in the human colon carcinoma cell line HT29. The three-carbon synthon (S)-glycidol was used for construction of the glycerol moiety. Glycosylation of (S)-glycidol with protected galactosyl and digalactosyl donors produced galactosyl and digalactosyl glycidols. Lewis acid catalyzed opening of the epoxide produced protected galactosyl and digalactosyl glycerolipids. Deprotection, or palmitoylation followed by deprotection, yielded the target compounds. The corresponding glycerolipid was synthesized analogously and an oxidation-reduction procedure for tritiation was developed. The synthesized compounds will be used in studies of the role of galactosyl glycerolipids in differentiation and colon cancer development. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00473-8

文献信息

• An efficient and convenient synthesis of deuterium-labelled seminolipid isotopomers and their ESI-MS characterization
  作者：Laura Franchini、Luigi Panza、Kessiri Kongmanas、Nongnuj Tanphaichitr、Kym F. Faull、Fiamma Ronchetti

  DOI：10.1016/j.chemphyslip.2008.02.002

  日期：2008.4

  Seminolipids 1a and 1b and galactosylalkylacylglycerols 2a and 2b, labelled with deuterium on the alkyl or acyl chain, respectively, were obtained isotopically and chemically pure through a straightforward synthesis from protected glycidyl galactoside 3 in an overall 22% yield. The identity and purity of compounds was ascertained by NMR spectroscopy and ESI mass spectrometry analysis. These labelled compounds

  通过从受保护的缩水甘油基半乳糖苷3进行直接合成，同位素和化学上纯净地分别获得了在烷基或酰基链上用氘标记的半脂质1a和1b以及半乳糖基烷基酰基甘油甘油2a和2b，总收率为22％。通过NMR光谱和ESI质谱分析确定化合物的身份和纯度。这些标记的化合物作为通过质谱定量这些脂质的内标非常重要，它们还可以用于体外甚至体内系统的代谢研究。程序的扩展可以为制备相同一般类别的其他化合物的同位素异构体提供一条途径。
• Synthesis of galactoglycerolipids found in the HT29 human colon carcinoma cell line
  作者：Jan Lindberg、Stefan C.T Svensson、Peter Påhlsson、Peter Konradsson

  DOI：10.1016/s0040-4020(02)00473-8

  日期：2002.6

  Synthesis of three galactoglycerolipids (3-O-(beta-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl)-1-O-hexadecyl-sn-glycerol), and the corresponding glycerolipid (1-O-hexadecyl-2-O-palmitoyl-sn-glycerol) is described. The first two compounds were recently identified in the human colon carcinoma cell line HT29. The three-carbon synthon (S)-glycidol was used for construction of the glycerol moiety. Glycosylation of (S)-glycidol with protected galactosyl and digalactosyl donors produced galactosyl and digalactosyl glycidols. Lewis acid catalyzed opening of the epoxide produced protected galactosyl and digalactosyl glycerolipids. Deprotection, or palmitoylation followed by deprotection, yielded the target compounds. The corresponding glycerolipid was synthesized analogously and an oxidation-reduction procedure for tritiation was developed. The synthesized compounds will be used in studies of the role of galactosyl glycerolipids in differentiation and colon cancer development. (C) 2002 Elsevier Science Ltd. All rights reserved.