3,4,6-tri-O-acetyl-α-D-galactopyranosyl 1,2-(tert-butyl orthoacetate) | 40147-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4,6-tri-O-acetyl-α-D-galactopyranosyl 1,2-(tert-butyl orthoacetate)
• 英文别名: 3,4,6-tri-O-acetyl-α-D-galactopyranose 1,2-(tert-butyl orthoacetate)；3,4,6-tri-O-acetyl-α-D-galactopyranose-1,2-(tert-butyl orthoacetate)；3,4,6-tri-O-acetyl-1,2-O-(tert-butylorthoacetyl)-α-D-galactopyranose；D-Galactose tert-butyl orthoester
• CAS: 40147-62-4
• 化学式: C₁₈H₂₈O₁₀
• 分子量: 404.414
• InChiKey: CPHHOBDQMIXIDV-QFVHWOIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  115.82
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-α-D-galactopyranosyl 1,2-(tert-butyl orthoacetate) 以 various solvent(s) 为溶剂， 反应 15.0h， 以4.5%的产率得到2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-lyxo-hex-1-enitol
  参考文献：
  名称：

  Grishina, I. I.; Andguladze, M. K.; Kaplun, A. P., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 481 - 484

  摘要：

  DOI：
• 作为产物：
  描述：

  叔丁醇 、 beta-D-半乳糖五乙酸酯 在 三氯化铝 、 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 26.75h， 以50%的产率得到1,2,3,4,6-戊-O-乙酰-a-D-吡喃半乳糖
  参考文献：
  名称：

  Syntheses of phosphatidyl-β-d-glucoside analogues to probe antigen selectivity of monoclonal antibody ‘DIM21’

  摘要：

  Herein, we report the chemical syntheses of a series of phosphatidyl-beta-D-glucoside (PtdGlc) analogues, including 6-O-Ac, sn-2-O-Me, phosphorothioate as well as phosphatidylgalactoside and -mannoside derivatives. In the key step, beta-glycosyl H-phosphonate was condensed with enantiomerically pure diacylglycerol. Comparison of spectroscopic data with mono-acetylated PtdGlc from natural source confirmed the presence of an acetyl moiety at position 6. Furthermore, the reactivity of PtdGlc and its analogues toward monoclonal antibody 'DIM21' (MAb DIM21) was evaluated, revealing the crucial structural antigen features for successful MAb DIM21 binding. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.041

文献信息

• Synthesis of acetylated glycosides of hydroxynaphthoquinones
  作者：S. G. Polonik、A. M. Tolkach、N. I. Uvarova

  DOI：10.1007/bf00579766

  日期：——

  A method is proposed for the synthesis of acetylated glycosides of hydroxynaphthoquinones. The condensation of D-glucose and D-galactose (tert-butyl orthoacetate)s with lawsone and lapachol has given the tetra-O-acetyl-β-D-glucopyranosides of lawsone and of lapachol and the tetra-O-acetyl-β-galactopyranoside of lawsone. The structures of the glycosides obtained have been confirmed by IR and1H and13C

  提出了一种合成羟基萘醌的乙酰化糖苷的方法。D-葡萄糖和 D-半乳糖（原乙酸叔丁酯）与 Lawsone 和 Lapachol 的缩合得到了 Lawsone 和 Lapachol 的四-O-乙酰基-β-D-吡喃葡萄糖苷和四-O-乙酰基-β-劳松的吡喃半乳糖苷。所得糖苷的结构已通过IR和1H和13C NMR光谱证实。先前描述的lawone 乙酰半乳糖苷的结构已得到纠正。
• Utkina, N. S.; Mal'tsev, S. D.; Danilov, L. L., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 5, p. 323 - 327
  作者：Utkina, N. S.、Mal'tsev, S. D.、Danilov, L. L.、Shibaev, V. N.

  DOI：——

  日期：——
• Evstigneeva, R. P.; Sebyakin, Yu. L.; Kalinina, E. V., Doklady Chemistry, 1992, vol. 325, # 4, p. 157 - 160
  作者：Evstigneeva, R. P.、Sebyakin, Yu. L.、Kalinina, E. V.、Kazakova, E. V.

  DOI：——

  日期：——
• Stereoselective synthesis of a ?-D-phosphatidylgalactose
  作者：N. G. Morozova、Yu. G. Sachkova、G. A. Serebrennikova、L. V. Volkova、R. P. Evstigneeva

  DOI：10.1007/bf00629822

  日期：——