(2R,3S,4R)-1,3,4-tris(benzyloxy)-5-nonen-2-ol | 500372-94-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4R)-1,3,4-tris(benzyloxy)-5-nonen-2-ol
• 英文别名: (2R,3S,4R)-1,3,4-tri-O-benzyl-5-nonene-1,2,3,4-tetraol；(2R,3S,4R)-1,3,4-tris(phenylmethoxy)non-5-en-2-ol
• CAS: 500372-94-1
• 化学式: C₃₀H₃₆O₄
• 分子量: 460.613
• InChiKey: QSIGAQBRMDALIH-OCBJUFRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-1,3,4-tris(benzyloxy)-5-nonen-2-ol 、 甲基磺酰氯 在 吡啶 作用下， 反应 18.0h， 以87%的产率得到(2R,3S,4R)-2-(methanesulfonyloxy)-1,3,4-tris(benzyloxy)-5-nonene
  参考文献：
  名称：

  RCAI-17, 22, 24–26, 29, 31, 34–36, 38–40, and 88, the analogs of KRN7000 with a sulfonamide linkage: Their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines

  摘要：

  RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 (1) with a sulfonamide linkage instead of an amide bond, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells. RCAI-17, 22, 24-26, 29, 31, 34-36, and 88 are the aromatic sulfonamide analogs, while RCAI-39 and 40 are the aliphatic ones. RCAI-38 is a C-galactoside analog of RCAI-26, which is the p-toluenesulfonamide analog of KRN7000. According to their bioassay, these sulfonamide analogs were shown to be the stimulants of mouse NKT cells to induce the production of Th2-biased cytokines in vitro, while RCAI-38 did not induce any cytokine production. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.060
• 作为产物：
  描述：

  丁基三苯基溴化膦 、 (2R,3S,4R)-2,3,5-tribenzyloxy-4-hydroxypentanal 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 19.5h， 以9.52 g的产率得到(2R,3S,4R)-1,3,4-tris(benzyloxy)-5-nonen-2-ol
  参考文献：
  名称：

  RCAI-17, 22, 24–26, 29, 31, 34–36, 38–40, and 88, the analogs of KRN7000 with a sulfonamide linkage: Their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines

  摘要：

  RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 (1) with a sulfonamide linkage instead of an amide bond, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells. RCAI-17, 22, 24-26, 29, 31, 34-36, and 88 are the aromatic sulfonamide analogs, while RCAI-39 and 40 are the aliphatic ones. RCAI-38 is a C-galactoside analog of RCAI-26, which is the p-toluenesulfonamide analog of KRN7000. According to their bioassay, these sulfonamide analogs were shown to be the stimulants of mouse NKT cells to induce the production of Th2-biased cytokines in vitro, while RCAI-38 did not induce any cytokine production. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.060

文献信息

• RCAI-17, 22, 24–26, 29, 31, 34–36, 38–40, and 88, the analogs of KRN7000 with a sulfonamide linkage: Their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines
  作者：Takuya Tashiro、Naomi Hongo、Ryusuke Nakagawa、Ken-ichiro Seino、Hiroshi Watarai、Yasuyuki Ishii、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.bmc.2008.08.060

  日期：2008.10

  RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 (1) with a sulfonamide linkage instead of an amide bond, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells. RCAI-17, 22, 24-26, 29, 31, 34-36, and 88 are the aromatic sulfonamide analogs, while RCAI-39 and 40 are the aliphatic ones. RCAI-38 is a C-galactoside analog of RCAI-26, which is the p-toluenesulfonamide analog of KRN7000. According to their bioassay, these sulfonamide analogs were shown to be the stimulants of mouse NKT cells to induce the production of Th2-biased cytokines in vitro, while RCAI-38 did not induce any cytokine production. (C) 2008 Elsevier Ltd. All rights reserved.