(2R,3R,4S)-1,3-O-isopropylidene-2,4-di-O-methylsulfonyl-5-hexen-1,2,3,4-tetrol | 501369-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S)-1,3-O-isopropylidene-2,4-di-O-methylsulfonyl-5-hexen-1,2,3,4-tetrol
• 英文别名: [(4R,5R)-2,2-dimethyl-4-[(1S)-1-methylsulfonyloxyprop-2-enyl]-1,3-dioxan-5-yl] methanesulfonate
• CAS: 501369-90-0
• 化学式: C₁₁H₂₀O₈S₂
• 分子量: 344.407
• InChiKey: OWOJMBPXSANLOS-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-1,3-O-isopropylidene-2,4-di-O-methylsulfonyl-5-hexen-1,2,3,4-tetrol 在 盐酸 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 31.0h， 生成 (2S,3R,4E)-2-叠氮-4-十八碳烯-1,3-二醇
  参考文献：
  名称：

  CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: synthesis of a family of sulfatides differing in the acyl chain moiety

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(02)01092-x
• 作为产物：
  描述：

  3,5-O-isopropylidene-D-xylofuranose 在 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (2R,3R,4S)-1,3-O-isopropylidene-2,4-di-O-methylsulfonyl-5-hexen-1,2,3,4-tetrol
  参考文献：
  名称：

  CD1a-binding glycosphingolipids stimulating human autoreactive T-cells: synthesis of a family of sulfatides differing in the acyl chain moiety

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(02)01092-x

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.