(R)-glycidyl-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside | 459432-38-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-glycidyl-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R)-oxiran-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 459432-38-3
• 化学式: C₃₇H₃₂O₁₁
• 分子量: 652.654
• InChiKey: PQSZHDJFECPVEY-QYUKHAPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (R)-glycidyl-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 1-O-hexadecyl-2-O-palmitoyl-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
• 作为产物：
  描述：

  ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside 、 (S)-缩水甘油 在 2,3,5-三甲基吡啶 、 4 A molecular sieve 、 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到(R)-glycidyl-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside
  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

• 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.