allyl 2,3-dideoxy-2,3-(N-p-toluenesulfonylepimino)-β-D-allopyranoside | 151895-57-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3-dideoxy-2,3-(N-p-toluenesulfonylepimino)-β-D-allopyranoside
• CAS: 151895-57-7
• 化学式: C₁₆H₂₁NO₆S
• 分子量: 355.412
• InChiKey: YKKXZDSSVHUBND-USUPDMAVSA-N

物化性质

• 沸点：
  560.8±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.02
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.07
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3-dideoxy-2,3-(N-p-toluenesulfonylepimino)-β-D-allopyranoside 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.75h， 生成 n-propyl 4,6-di-O-acetyl-3-S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-deoxy-3-thio-2-p-toluenesulfonamido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of α-L-fucopyranosyl disaccharides with thioglycosidic linkages and characterization of α-L-fucosidases from bovine kidney and epididymis by their inhibitory activities

  摘要：

  Sulfur-linked disaccharide analogs of three alpha-L-fucopyranosyl 2-acetamido-2-deoxy-beta-D-glucopyranosides and one alpha-L-fucopyranosyl beta-D-galactopyranoside were synthesized by substitution reactions of sulfonates and ring-opening reactions of aziridine as well as oxirane derivatives using 1-thio-alpha-L-fucopyranose as nucleophile. Fucosidases from bovine kidney and epididymis were inhibited by all of these disaccharide analogs and their Ki values range from 0.65 to 4.9 mM.

  DOI：

  10.1016/s0957-4166(00)80385-7
• 作为产物：
  描述：

  allyl 4,6-O-benzylidene-2,3-dideoxy-2,3-epimino-β-D-allopyranoside 在 吡啶 、 Dowex 50W-X₂ (H+) 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 allyl 2,3-dideoxy-2,3-(N-p-toluenesulfonylepimino)-β-D-allopyranoside
  参考文献：
  名称：

  Synthesis of α-L-fucopyranosyl disaccharides with thioglycosidic linkages and characterization of α-L-fucosidases from bovine kidney and epididymis by their inhibitory activities

  摘要：

  Sulfur-linked disaccharide analogs of three alpha-L-fucopyranosyl 2-acetamido-2-deoxy-beta-D-glucopyranosides and one alpha-L-fucopyranosyl beta-D-galactopyranoside were synthesized by substitution reactions of sulfonates and ring-opening reactions of aziridine as well as oxirane derivatives using 1-thio-alpha-L-fucopyranose as nucleophile. Fucosidases from bovine kidney and epididymis were inhibited by all of these disaccharide analogs and their Ki values range from 0.65 to 4.9 mM.

  DOI：

  10.1016/s0957-4166(00)80385-7

文献信息

• Synthesis of 1→6,1→4 and 1→3 linked 1-thio-α-L-fucopyranosyl 2-acetamido-2-deoxy-β-D-glucopyranosides and 1→2 linked β-D-galactopyranoside, and their linkage-specific inhibitory activities toward α-L-fucosidases
  作者：Hironobu Hashimoto、Kazuya Shimada、Shigeomi Horito

  DOI：10.1016/s0040-4039(00)74055-x

  日期：1993.7

  Sulfur-linked disaccharides analogs of three α-L-fucopyranosyl 2-acetamido-2-deoxy-β-D-gluco pyranosides and one α-L-fucopyranosyl β-D-galactopyranoside were synthesized by substitution reactions of sulfonates and ring-opening reactions of aziridine as well as oxirane derivatives using 1-thio-α-L-fucopyranose derivative as nucleophile. Fucosidases from bovine kidney and epididymis were inhibited by

  通过磺酸盐的取代反应和开环反应，合成了三种α-L-呋喃二糖基2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷和一种α-L-呋喃二糖基β-D-吡喃半乳糖苷的硫连接二糖类似物。 1-硫代-α-L-呋喃琼脂糖衍生物作为亲核试剂测定氮丙啶和环氧乙烷衍生物。所有这些二糖类似物均抑制了来自牛肾和附睾的岩藻糖苷酶，其Ki值范围为0.65至4.9 mM。