methyl 6-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 172975-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS: 172975-24-5
• 化学式: C₄₂H₅₀O₁₅
• 分子量: 794.85
• InChiKey: BMRABXMMHJKLNO-FBHJKXNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  57.0
• 可旋转键数：
  19.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  169.81
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl 6-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以124 mg的产率得到methyl β-D-galactofuranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of galactofuranose-containing disaccharides using thioimidoyl-type donors

  摘要：

  Four galactofuranose-containing disaccharides have been prepared utilising various thioimidates [Galf-SC(=NR)XR'] and suitably protected acceptors as key precursors. We observed that the efficiency of the coupling reactions was particularly dependent on the aglycon present on the furanosyl donor when copper(II) ions were used as the promoter, and that activation could be correlated with the nature of the third heteroatorn, X. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.001
• 作为产物：
  描述：

  1,2,3,5,6-penta-O-acetyl-D-galactofuranose 在 三氟化硼乙醚 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 6-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of galactofuranose-containing disaccharides using thioimidoyl-type donors

  摘要：

  Four galactofuranose-containing disaccharides have been prepared utilising various thioimidates [Galf-SC(=NR)XR'] and suitably protected acceptors as key precursors. We observed that the efficiency of the coupling reactions was particularly dependent on the aglycon present on the furanosyl donor when copper(II) ions were used as the promoter, and that activation could be correlated with the nature of the third heteroatorn, X. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.001

文献信息

• A convenient synthesis of disaccharides containing furanoside units
  作者：Rachel Velty、Thierry Benvegnu、Muriel Gelin、Eric Privat、Daniel Plusquellec

  DOI：10.1016/s0008-6215(96)00268-6

  日期：1997.3

  Abstract Pent-4-enyl 2,3,5,6-tetra-O-acetyl- d -glycofuranosides were synthesized in a one-pot reaction by a ferric chloride-promoted glycosylation of 4-penten-1-ol with d -glucose, d -mannose, and d -galactose, respectively, in heterogeneous media, followed by in situ acetylation. These n -pentenyl glycosides are efficient glycofuranosyl donors and have therefore been used for the subsequent synthesis

  摘要通过氯化铁促进4-戊烯-1-醇与d-葡萄糖的一锅反应，合成了Pent-4-enyl 2,3,5,6-tetra-O-acetyl- d-糖呋喃糖苷。 ，分别在异质培养基中添加d-甘露糖和d-半乳糖，然后进行原位乙酰化。这些正戊烯基糖苷是有效的呋喃呋喃糖基供体，因此已用于随后合成与古细菌糖脂和原生动物糖缀合物有关的各种呋喃糖基-吡喃糖苷型或呋喃糖基-呋喃糖苷型二糖。
• n-Pentenyl furanosides: synthesis and glycosidation reactions of some galacto derivatives
  作者：Ashok Arasappan、Bert Fraser-Reid

  DOI：10.1016/0040-4039(95)01718-w

  日期：1995.10

  Synthetic routes to n-pentenyl galactofuranosides and glycosidation reactions of some derived donors with alcohol and saccharide acceptors using NIS/TESOTf as the promoter are described.

  描述了使用NIS / TESOTf作为促进剂的合成正戊烯基半乳糖呋喃糖苷的合成路线以及一些衍生的供体与醇和糖受体的糖基化反应。