phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside | 227749-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside
• CAS: 227749-88-4
• 化学式: C₈₈H₇₉NO₁₉S
• 分子量: 1486.66
• InChiKey: LALJQYCUDQKOBH-NVBLODITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.92
• 重原子数：
  109.0
• 可旋转键数：
  29.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  225.65
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 、 11-tris(3,7,11,15-tetramethylhexadecyloxymethyl)-3,6,9-trioxa-1-undecanol 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到11-tris(3,7,11,15-tetramethylhexadecyloxymethyl)-3,6,9-trioxa-1-undecyl-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  新型高度疏水性路易斯 X 糖脂：合成和单层行为

  摘要：

  制备了两种高度疏水的路易斯 X 糖脂 2 和 3。糖缀合物 2 以下列方式构建：季戊四醇用作分配器，其上的三个外消旋植醇疏水链和一个三甘醇间隔基用五糖 Gal (β 1-4)[Fuc (α 1-3)] GlcNAc β-糖基化(β 1-3) Gal (β 1-4) Glc 被锚定。糖缀合物 3 以类似的方式构建，糖部分是三糖 Gal (β 1-4)[Fuc (α 1-3)] GlcNAc，即所谓的 Lewis X 决定簇。使用三甘醇间隔物以引入研究单一碳水化合物-碳水化合物相互作用所需的流动性。与天然神经酰胺糖脂 1 相比，三个植基链增加了脂质部分的疏水性。这些糖脂在单层研究中显示出具有高压缩性的液体膨胀行为。这些与在水中的低溶解度相关的特性使它们成为研究两个 Lewis X 功能化囊泡之间相互作用的良好候选者。

  DOI：

  10.1002/1099-0690(200101)2001:2<253::aid-ejoc253>3.0.co;2-2
• 作为产物：
  描述：

  1-硫-乙基-2,3,4-三-氧-苄基-b-L-硫代呋喃岩藻糖苷 、 phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以86%的产率得到phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the β-Methyl Glycoside of Lacto-N-Fucopentaose III

  摘要：

  A total synthesis of the beta-methyl glycoside of lacto-N-fucopentaose III (1) is described. Phenyl 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1-->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (4), a key intermediate prepared by condensation of 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl bromide (2) and phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside (3), was glycosylated with ethyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside (5) to give the trisaccharide donor 6, which, on coupling with methyl 2,6-di-O-benzyl-beta-D-galactopyranosyl-(1-->4)2,3,6-tri-O-benzyl-beta-D-glucopyranoside (7), afforded the pentasaccharide 8. It was easily transformed into the target pentasaccharide 1 via hydrazinolysis, acetylation, O-deacetylation, and hydrogenolysis.

  DOI：

  10.1080/07328309908544006

文献信息

• NMR study of a LewisX pentasaccharide derivative: solution structure and interaction with cations
  作者：Benoı̂t Henry、Hervé Desvaux、Marina Pristchepa、Patrick Berthault、Yong-Min Zhang、Jean-Maurice Mallet、Jacques Esnault、Pierre Sinaÿ

  DOI：10.1016/s0008-6215(98)00301-2

  日期：1999.1

  The structure and conformation of the synthetic pentasaccharide Gal(beta 1-4)Fuc(alpha 1-3)}GlcNAc(beta 1-3)Gal(beta 1-4)Glc-beta OMe of the Lewis(x) family has been determined by NMR spectroscopy in dimethyl sulfoxide and methanol. In these solvents, the binding constants with calcium have been evaluated as 9.5 and 29.6 M-1, respectively. Study of the interaction sites has been achieved through the use of paramagnetic divalent cations and distance triangulation methods. Two regions have been found, the first one in the vicinity of the fucose unit, the second one closer to the lactose part. (C) 1999 Elsevier Science Ltd. All rights reserved.
• The Natural Lewis^X-Bearing Lipids Promote Membrane Adhesion: Influence of Ceramide on Carbohydrate-Carbohydrate Recognition
  作者：Christine Gourier、Frédéric Pincet、Eric Perez、Yongmin Zhang、Zhenyuan Zhu、Jean-Maurice Mallet、Pierre Sinaÿ

  DOI：10.1002/anie.200461224

  日期：2005.3.4