2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl isothiocyanate | 198271-81-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl isothiocyanate
• 英文别名: [(2R)-2-benzoyloxy-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-isothiocyanatooxolan-2-yl]ethyl] benzoate
• CAS: 198271-81-7
• 化学式: C₃₅H₂₇NO₉S
• 分子量: 637.667
• InChiKey: SPNPQWUVIKXTRS-GGEKVXJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl isothiocyanate 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 生成 [(2R)-2-benzoyloxy-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-(2-sulfanylidene-1H-imidazol-3-yl)oxolan-2-yl]ethyl] benzoate
  参考文献：
  名称：

  Synthesis of β-d-galactofuranosyl nucleoside analogues. A new type of β-d-galactofuranosidase inhibitor

  摘要：

  The development of beta -D-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because beta -D-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared beta -D-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated beta -D-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-beta -D-Galactofuratlosyl-O-ethylthiourethane N-beta -D-galactofuranosyl-4-oxoimidazolidi N-beta -D-galactofuranosyl-4-imidazoline-2-thione, and N-beta -D-galactofuranosyl-4-methoxyimidazolidine-2-thione, were prepared. The biological assays showed that imidazoline and imidazolidine-2-thione derivatives act as a new type of exo beta -D-galactofuranosidase inhibitor. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00146-x
• 作为产物：
  描述：

  1,2,3,5,6-penta-O-benzoyl-D-galactofuranose 在 盐酸 、 乙酰氯 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl isothiocyanate
  参考文献：
  名称：

  糖呋喃糖基异硫氰酸酯的简便合成

  摘要：

  摘要在正常条件下，由无水丙酮中的硫氰酸钾与相应的糖基氯反应，可在相应的糖基氯条件下，在光滑的条件下，于平滑的条件下获得过酰基化的呋喃呋喃糖基异硫氰酸酯，这是糖基吡喃糖基硫氰酸酯合成的经典条件。在呋喃糖酶的情况下，没有获得糖基硫氰酸酯，并且该方法立体选择性地产生1，2-反式异硫氰酸酯，产率超过80％。

  DOI：

  10.1016/s0008-6215(97)00242-5

文献信息

• Reactions of per-O-benzoyl-β-D-Galf isothiocyanate, a chiral resolving agent
  作者：Carla Marino、Oscar Varela、Rosa M. de Lederkremer

  DOI：10.1016/s0040-4020(97)10070-9

  日期：1997.11

  Tetra-O-benzoyl-beta-D-galactofuranosyl isothiocyanate (1) was readily prepared (90% yield) from per-O-benzoyl-D-galactofuranose, via the glycosyl bromide. Reaction of 1 with alcohols, amines and amino acids afforded a variety of glycosylthiourethanes and glycosylthioureides. The isothiocyanate 1 showed to be useful as a chiral resolving agent. The resolution of racemic primary and secondary amines and aminoalcohols was readily accomplished, in analytical and preparative scale, by condensation of such compounds with 1. (C) 1997 Elsevier Science Ltd.
• Facile synthesis of glycofuranosyl isothiocyanates
  作者：Carla Marino、Oscar Varela、Rosa M de Lederkremer

  DOI：10.1016/s0008-6215(97)00242-5

  日期：1997.11

  Abstract Peracylated glycofuranosyl isothiocyanates are obtained under smooth conditions starting from the corresponding glycosyl chloride by reaction with potassium thiocyanate in anhydrous acetone at room temperature, classical conditions for the synthesis of glycopyranosyl thiocyanates. In the case of furanoses, no glycosyl thiocyanates are obtained, and the procedure leads to the 1,2- trans isothiocyanates

  摘要在正常条件下，由无水丙酮中的硫氰酸钾与相应的糖基氯反应，可在相应的糖基氯条件下，在光滑的条件下，于平滑的条件下获得过酰基化的呋喃呋喃糖基异硫氰酸酯，这是糖基吡喃糖基硫氰酸酯合成的经典条件。在呋喃糖酶的情况下，没有获得糖基硫氰酸酯，并且该方法立体选择性地产生1，2-反式异硫氰酸酯，产率超过80％。
• Synthesis of β-d-galactofuranosyl nucleoside analogues. A new type of β-d-galactofuranosidase inhibitor
  作者：Carla Marino、Pal Herczegh、Rosa M de Lederkremer

  DOI：10.1016/s0008-6215(01)00146-x

  日期：2001.7

  The development of beta -D-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because beta -D-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared beta -D-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated beta -D-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-beta -D-Galactofuratlosyl-O-ethylthiourethane N-beta -D-galactofuranosyl-4-oxoimidazolidi N-beta -D-galactofuranosyl-4-imidazoline-2-thione, and N-beta -D-galactofuranosyl-4-methoxyimidazolidine-2-thione, were prepared. The biological assays showed that imidazoline and imidazolidine-2-thione derivatives act as a new type of exo beta -D-galactofuranosidase inhibitor. (C) 2001 Elsevier Science Ltd. All rights reserved.