1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-(benzyloxycarbonyl)imino-D-glycero-L-galacto-heptitol | 856174-72-6

• 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: 1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-(benzyloxycarbonyl)imino-D-glycero-L-galacto-heptitol
• 英文别名: benzyl (2R,3S,4R,5S,6R)-2-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidine-1-carboxylate
• CAS: 856174-72-6
• 化学式: C₄₃H₄₅NO₇
• 分子量: 687.833
• InChiKey: NZAKSMMAJBVNNR-LLGAQKOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-(benzyloxycarbonyl)imino-D-glycero-L-galacto-heptitol 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 benzyl (2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(3-hydroxy-3-oxoprop-1-en-1-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  含氨基糖的KRN7000类似物的合成

  摘要：

  设计并合成了三种新的含亚氨基糖的KRN7000（也称为α- GalCer）类似物。在设计中，用亚氨基糖代替了KRN7000的半乳糖部分，亚氨基糖的结构以不同的方式通过C糖苷键而不是O糖苷键与神经酰胺连接。据我们所知，这是第一个将亚氨基糖掺入KRN7000结构修饰的报道。评价合成化合物刺激细胞因子释放的能力。结果可能有助于更好地了解结构-活性关系，并有助于将来设计更多的KRN7000衍生物。

  DOI：

  10.1002/cjoc.201600862
• 作为产物：
  描述：

  1,2,6-trideoxy-6-<<(phenylmethoxy)carbonyl>amino>-3,4,5,7-tetrakis-O-(phenylmethyl)-D-gluco-hept-1-enitol 生成 1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-(benzyloxycarbonyl)imino-D-glycero-L-galacto-heptitol
  参考文献：
  名称：

  LIU, PAUL S., J. ORG. CHEM., 52,(1987) N 21, 4717-4721

  摘要：

  DOI：

文献信息

• Concise syntheses of selective inhibitors against α-1,3-galactosyltransferase
  作者：Guo-Liang Zhang、Li-He Zhang、Xin-Shan Ye

  DOI：10.1039/c0ob00042f

  日期：——

  Several iminosugar-based uridine diphosphate galactose (UDP-Gal) mimetics 1–4 including D- and L-epimers were designed and synthesized by concise routes, and these synthetic compounds were evaluated for the inhibition of α-1,3- and β-1,4-galactosyltransferases in vitro. The experimental data demonstrated that L-epimer 2 displayed the strongest inhibitory activity with moderate selectivity against α-1,3-galactosyltransferase.

  通过简洁的路线设计和合成了几种亚氨基糖基二磷酸尿苷半乳糖（UDP-Gal）模拟物1â4，包括D-表聚体和L-表聚体，并在体外评估了这些合成化合物对δ-1,3-和δ-1,4-半乳糖基转移酶的抑制作用。实验数据表明，L-表聚物 2 对δ-1,3-半乳糖基转移酶具有最强的抑制活性和适度的选择性。
• Synthetic Iminosugar Derivatives as New Potential Immunosuppressive Agents
  作者：Xin-Shan Ye、Fang Sun、Min Liu、Qin Li、Yuhang Wang、Guisheng Zhang、Li-He Zhang、Xiao-Lian Zhang

  DOI：10.1021/jm050169t

  日期：2005.6.1

  Several iminosugar derivatives were synthesized, and their effects on the secretion of IL-4 and IFN-gamma from the mouse splenocytes were examined. The effects on membrane expression of other T cell-associated molecules (CD3, CD4, CD8) and B cell-associated molecules (CD19) were also investigated. The experimental data demonstrated that synthetic iminosugars hold potential as immunosuppressive agents.
• Synthesis of N-substituted iminosugar derivatives and their immunosuppressive activities
  作者：Guo-Liang Zhang、Changshui Chen、Yulan Xiong、Li-He Zhang、Jia Ye、Xin-Shan Ye

  DOI：10.1016/j.carres.2010.01.021

  日期：2010.4

  Several N-alkyl and hydroxyethyl-substituted iminosugar derivatives, including L-altro and D-galacto epimers, were synthesized and the effects of these synthetic iminosugars on proliferation of mouse splenocytes were evaluated in the MTT assay. The experimental data demonstrated that the N-alkylated D-galacto iminosugars showed better inhibitory activities than L-altro analogues, which might hold potential as immunosuppressive agents. (C) 2010 Elsevier Ltd. All rights reserved.