(2S,3S,4R)-2-amino-1,3,4-tris(tert-butyldimethylsilyloxy)nonane | 1082745-96-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3S,4R)-2-amino-1,3,4-tris(tert-butyldimethylsilyloxy)nonane
• CAS: 1082745-96-7
• 化学式: C₂₇H₆₃NO₃Si₃
• 分子量: 534.059
• InChiKey: MBTLFYYGQZXACA-VXNXHJTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  34.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  二十酸 、 (2S,3S,4R)-2-amino-1,3,4-tris(tert-butyldimethylsilyloxy)nonane 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以86%的产率得到N-((6S,7S,8R)-7-((tert-butyldimethylsilyl)oxy)-2,2,3,3,10,10,11,11-octamethyl-8-pentyl-4,9-dioxa-3,10-disiladodecan-6-yl)icosanamide
  参考文献：
  名称：

  Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH

  摘要：

  An alpha-galactosyl ceramide (alpha-GalCer) 2 was synthesized and evaluated for its ability to stimulate iNKTcell proliferation and elicit T-helper cytokines, IL-4 and IFN gamma. Compound 2 combines the acyl chain of the potent, Th2 biasing alpha-GalCer 1 with a sphingoid base of the same length as that found in OCH, which also exhibits Th2 skewing, Such complementation may enhance cytokine bias, which is thought to be important for therapeutic applications of iNKT cell stimulation. Two related alpha-GalCers, 3 and 4, with saturated acyl chains were prepared for comparison. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.042
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 (2S,3S,4R)-2-amino-1,3,4-nonanetriol 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以1.74 g的产率得到(2S,3S,4R)-2-amino-1,3,4-tris(tert-butyldimethylsilyloxy)nonane
  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