[(2R,3S,4S,5R,6S)-3,4-diacetyloxy-5-[chloro(dimethyl)silyl]oxy-6-phenylsulfanyloxan-2-yl]methyl acetate | 153439-89-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3S,4S,5R,6S)-3,4-diacetyloxy-5-[chloro(dimethyl)silyl]oxy-6-phenylsulfanyloxan-2-yl]methyl acetate
• CAS: 153439-89-5
• 化学式: C₂₀H₂₇ClO₈SSi
• 分子量: 491.034
• InChiKey: SBLOFNFAQQMZSM-CXQPBAHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4-diacetyloxy-5-[chloro(dimethyl)silyl]oxy-6-phenylsulfanyloxan-2-yl]methyl acetate 在 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 、 硝基甲烷 为溶剂， 反应 19.5h， 生成 methyl 2,6-di-O-benzyl-4,2'-di-O-dimethylsilylene-3-O-(3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient stereocontrolled glycosidation of secondary sugar hydroxyls by silicon tethered intramolecular glycosidation

  摘要：

  Dissaccharides containing 1.2-cis glycoside linkages were synthesized by an efficient stereocontrolled two step process involving a silicon tethering step, to a dimethylsilyl acetal followed by intramolecular glycosidation with N-iodosuccinimide in nitromethane.

  DOI：

  10.1016/s0040-4020(01)80200-3
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-β-D-galactopyranosyl chloride 在 吡啶 作用下， 以 甲苯 为溶剂， 生成 [(2R,3S,4S,5R,6S)-3,4-diacetyloxy-5-[chloro(dimethyl)silyl]oxy-6-phenylsulfanyloxan-2-yl]methyl acetate
  参考文献：
  名称：

  Application of intramolecular glycosidation to the stereocontrolled synthesis of disaccharides containing α-gluco and α-galacto linkages

  摘要：

  含有α-葡萄糖和α-半乳糖连接键的二糖通过一种二甲基硅基连接的中间体的分子内糖苷化反应，从初级和次级糖羟基及2-羟基硫糖苷特异性合成。

  DOI：

  10.1039/c39930000791

文献信息

• Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide
  作者：Natacha Veerapen、Manfred Brigl、Salil Garg、Vincenzo Cerundolo、Liam R. Cox、Michael B. Brenner、Gurdyal S. Besra

  DOI：10.1016/j.bmcl.2009.05.095

  日期：2009.8

  We herein report a faster and less cumbersome synthesis of the biologically attractive, α-galactosyl ceramide (α-GalCer), known as KRN7000, and its analogues. More importantly, the use of a silicon tethered intramolecular glycosylation reaction gave easy access to the diglycosyl ceramide Gal(α1→2)GalCer, which has been shown to require uptake and processing to the biologically active α-GalCer derivative

  我们在此报告了具有生物学吸引力的 α-半乳糖神经酰胺 (α-GalCer)（称为 KRN7000）及其类似物的更快、更简便的合成。更重要的是，使用硅系链分子内糖基化反应可以轻松获得二糖基神经酰胺 Gal(α1 → 2)GalCer，其已被证明需要摄取和加工成具有生物活性的 α-GalCer 衍生物。
• Ceramide derivatives as modulators of immunity and autoimmunity
  申请人：Porcelli A. Steven

  公开号：US20060052316A1

  公开（公告）日：2006-03-09

  α-Galactosylceramides and glycosylceramides (“ceramide-like glycolipids”) that modulate NK T cells. The ceramide-like glycolipids vary in the cytokines induced in NK T cells and vary in the antigen-presenting cells that are capable of efficiently presenting the compounds to NK T cells. Pharmaceutical compositions of the ceramide-like glycolipids are provided, as are pharmaceutical compositions of the ceramide-like glycolipids combined with dendritic cells. Methods utilizing the ceramide-like glycolipids in vaccines, to activate NK T cells, to stimulate the immune system, and to treat mammals are also provided. The invention also provides methods of evaluating a compound for its ability to activate an NK T cell in the presence of a cell expressing a CD1d protein.

  α-半乳糖基神经酰胺和糖基神经酰胺（“类神经酰胺糖脂”），调节NK T细胞。这些类神经酰胺糖脂在NK T细胞中诱导的细胞因子中有所不同，并且在有效呈递这些化合物给NK T细胞的抗原呈递细胞中也有所不同。提供了含有类神经酰胺糖脂的药物组合物，以及与树突状细胞结合的类神经酰胺糖脂的药物组合物。还提供了利用这些类神经酰胺糖脂制备疫苗、激活NK T细胞、刺激免疫系统和治疗哺乳动物的方法。本发明还提供了评估化合物在表达CD1d蛋白的细胞存在下激活NK T细胞能力的方法。