(2S,3R,4E)-1-(α-D-galactopyranosyloxy)-2-(docosanoylamino)-3-hydroxy-4-octadecene | 74645-25-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R,4E)-1-(α-D-galactopyranosyloxy)-2-(docosanoylamino)-3-hydroxy-4-octadecene
• 英文别名: (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(docosanoylamino)-3-hydroxyoctadec-4-ene；1-(beta-D-galactosyl)-N-behenoylsphingosine；N-[(E,2S,3R)-3-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]docosanamide
• CAS: 74645-25-3
• 化学式: C₄₆H₈₉NO₈
• 分子量: 784.215
• InChiKey: YIGARKIIFOHVPF-YMBRMJIUSA-N

物化性质

• 沸点：
  887.4±65.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  55
• 可旋转键数：
  39
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-1-(α-D-galactopyranosyloxy)-2-(docosanoylamino)-3-hydroxy-4-octadecene 在 二正丁基氧化锡 、 三甲基铵三氧化硫共聚物 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 4.0h， 以70%的产率得到(2S,3R,4E)-1-[3-O-(sodium oxysulfonyl)-β-D-galactopyranosyloxy]-2-(docosanoylamino)-3-hydroxyoctadec-4-ene
  参考文献：
  名称：

  Synthesis and evaluation of human T cell stimulating activity of an α-sulfatide analogue

  摘要：

  A concise synthesis of alpha-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the alpha-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated beta-GalCer (sulfatide) and alpha-GalCer, which activate specific T cells. alpha-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than alpha-GalCer, while it was not recognized by CD1a-restricted sulfatide-specific T cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.044
• 作为产物：
  描述：

  (2S,3R,4E)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-(docosanoylamino)-3-hydroxy-4-octadecene 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (2S,3R,4E)-1-(α-D-galactopyranosyloxy)-2-(docosanoylamino)-3-hydroxy-4-octadecene
  参考文献：
  名称：

  Synthesis and evaluation of human T cell stimulating activity of an α-sulfatide analogue

  摘要：

  A concise synthesis of alpha-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the alpha-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated beta-GalCer (sulfatide) and alpha-GalCer, which activate specific T cells. alpha-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than alpha-GalCer, while it was not recognized by CD1a-restricted sulfatide-specific T cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.044

文献信息

• CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: synthesis of a family of sulfatides differing in the acyl chain moiety
  作者：Federica Compostella、Laura Franchini、Gennaro De Libero、Giovanni Palmisano、Fiamma Ronchetti、Luigi Panza

  DOI：10.1016/s0040-4020(02)01092-x

  日期：2002.10

  Native sulfatide (a mixture of 3-sulfated beta-D-galactopyranosylceramides with different fatty acids at the ceramide moiety) is an antigen presented by CD1a proteins. Herein the preparation of four sulfatides, which are constituents of the natural mixture and bear palmitic, stearic, behenic or nervonic fatty acid chains, is described. Azidosphingosine was stereoselectively synthesized through a CuCN-catalyzed allylic alkylation of a hexenitol dimesylate derived from D-xylose; beta-glycosylation of azidosphingosine, with a suitable D-galactosyl trichloroacetimidate led, after reduction of the azido, group, to the galactosylsphingosine skeleton, which was derivatized with the different fatty acids. Final regioselective 3-sulfation gave the desired sulfatides, which were tested for activation of sulfatide-specific and CD1a-restricted T-cell clones. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and evaluation of human T cell stimulating activity of an α-sulfatide analogue
  作者：Laura Franchini、Pamela Matto、Fiamma Ronchetti、Luigi Panza、Lucia Barbieri、Valeria Costantino、Alfonso Mangoni、Marco Cavallari、Lucia Mori、Gennaro De Libero

  DOI：10.1016/j.bmc.2007.05.044

  日期：2007.8

  A concise synthesis of alpha-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the alpha-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated beta-GalCer (sulfatide) and alpha-GalCer, which activate specific T cells. alpha-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than alpha-GalCer, while it was not recognized by CD1a-restricted sulfatide-specific T cells. (c) 2007 Elsevier Ltd. All rights reserved.