S-Benzyl-β-mercaptopropionsaeure-N-hydroxysuccinimidester | 3481-24-1

• 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: S-Benzyl-β-mercaptopropionsaeure-N-hydroxysuccinimidester
• CAS: 3481-24-1
• 化学式: C₁₄H₁₅NO₄S
• 分子量: 293.343
• InChiKey: WFRREBBWSPRBMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  S-Benzyl-β-mercaptopropionsaeure-N-hydroxysuccinimidester 、 2-aminoethyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以69%的产率得到3-benzylsulfanyl-N-[2-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]propanamide
  参考文献：
  名称：

  Synthesis of some divalent O- and S-glycosides of galabiose and globotriose

  摘要：

  Derivatives of galabiose (alpha-D-Galp-(1-->4)-D-Galp) and globotriose (alpha-D-Galp-(1-->4)-beta-D-Galp(1-->4)-D-Glcp) were coupled to various 1,2- and 1,3-dihydroxymethyl- and dimercaptomethylbenzenes to give the corresponding divalent glycosides, potentially useful as inhibitors of bacterial adhesion. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00021-4
• 作为产物：
  描述：

  苄硫醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 S-Benzyl-β-mercaptopropionsaeure-N-hydroxysuccinimidester
  参考文献：
  名称：

  Di-, Tri-, and Tetravalent Dendritic Galabiosides That Inhibit Hemagglutination by Streptococcus suis at Nanomolar Concentration

  摘要：

  Galabiose (Gal alpha 1-4Gal) derivatives were coupled to carrier molecules having mono-, di-, tri-, and tetrameric functionalities, thus creating mono- to tetravalent dendritic galabiosides (1-9). The di- to tetravalent galabiosides were several hundred times more efficient than the monomeric galabiosides in inhibiting hemagglutination by the Gram-positive bacterium Streptococcus suis, resulting in complete inhibition at low nanomolar concentrations. This is unprecedented in the field of inhibition of bacterial adhesion by soluble compounds.

  DOI：

  10.1021/ja970859p