methyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate | 400888-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate
• CAS: 400888-43-9
• 化学式: C₃₇H₄₀O₈
• 分子量: 612.72
• InChiKey: FLMKLOYPTKMGIK-VCPMIQRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  45.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate 在 palladium on carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以100%的产率得到methyl 2-((2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetate
  参考文献：
  名称：

  Assessing the ability of a short fluorinated antifreeze glycopeptide and a fluorinated carbohydrate derivative to inhibit ice recrystallization

  摘要：

  A short fluorinated antifreeze glycopeptide (2) was synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The activity of 2 was compared to native biological antifreeze AFGP 8 and a rationally designed C-linked AFGP analogue (OGG-Gal, 1). In addition, a simple fluorinated galactose derivative was prepared and its IRI activity was compared to non-fluorinated compounds. The results from this study suggest that the stereochemistry at the anomeric position in the carbohydrate plays a role in imparting ice recrystallization inhibition activity and that incorporation of hydrophobic groups such as fluorine atoms cause a decrease in IRI activity. These observations are consistent with the theory that fluorine atoms increase ordering of bulk water resulting in a decrease of IRI activity, supporting our previously proposed mechanism of ice recrystallization inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.148
• 作为产物：
  描述：

  ((2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester 在 caesium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 methyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate
  参考文献：
  名称：

  Synthesis of Sugar-fused GABA-analogs

  摘要：

  γ-氨基丁酸（GABA）-糖类类似物以C-酮苷的形式可以从d-或l-葡萄糖内酯和d-半乳糖内酯出发，通过4到7个步骤合成。合成的关键步骤是以三甲基氟甲基磺酸酯（TMS-OTf）促进的2-脱氧-3-呋喃糖酸与三甲基氰化物的C-糖苷化反应。通过氢化得到的β-氰酯可以提供GABA类似物，这些类似物是在糖骨架上表现的。

  DOI：

  10.1055/s-2001-18097

文献信息

• Synthesis of a galacto-configured C-ketoside-based γ-sugar-amino acid and its use in peptide coupling reactions
  作者：Frank Schweizer、Ole Hindsgaul

  DOI：10.1016/j.carres.2006.03.006

  日期：2006.7

  gamma-Sugar-amino acid analogues in the form of C-ketosides can be prepared in 5-6 steps starting from D-galactono-1,5-lactone. The key step in the synthesis is the trimethylsilyl trifluoromethanesulfonate (TMSOTf) promoted C-glycosylation of 2-deoxy-3-ulopyranosonates with trimethylsilyl cyanide. Hydrogenation of the resulting beta-cyano esters provides C-ketoside-based gamma-sugar-amino acids that serve as building blocks for the synthesis of unnatural neoglycopeptides. (c) 2006 Elsevier Ltd. All rights reserved.