1,3-O-benzylidene-2-O-methanesulfonyl-4-O-p-nitrobenzoyl-D-arabino-1,2,3,4-nonanetetrol | 1333920-08-3

• 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-O-benzylidene-2-O-methanesulfonyl-4-O-p-nitrobenzoyl-D-arabino-1,2,3,4-nonanetetrol
• 英文别名: [(1R)-1-[(2S,4R,5R)-5-methylsulfonyloxy-2-phenyl-1,3-dioxan-4-yl]hexyl] 4-nitrobenzoate
• CAS: 1333920-08-3
• 化学式: C₂₄H₂₉NO₉S
• 分子量: 507.562
• InChiKey: IPXBUQGFDXTACF-AZKZNFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3-O-benzylidene-2-O-methanesulfonyl-4-O-p-nitrobenzoyl-D-arabino-1,2,3,4-nonanetetrol 在 甲醇 、 sodium methylate 、 水 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以84%的产率得到(2R,3S,4R)-1,3-O-benzylidene-2-O-methanesulfonyl-1,2,3,4-nonanetetrol
  参考文献：
  名称：

  Synthesis of α-S-galactosylceramides with a truncated sphingoid chain

  摘要：

  We present here a convenient synthesis of the truncated sphingoid iodide 15 from D-galactose, in which Mitsunobu reaction was utilized to retrieve successfully an unwanted intermediate, thereby increasing greatly the synthetic efficiency. Subsequent reaction of 15 with the pre-prepared alpha-galactosyl thiol 16 led smoothly to the desired thioglycoside 17 in good yield, from which the catabolically stable thioglycoside analogs of OCH 4 and 22 were synthesized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.103
• 作为产物：
  描述：

  2,4-O-benzylidene-D-threose 在 吡啶 、 偶氮二甲酸二异丙酯 、 magnesium 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1,3-O-benzylidene-2-O-methanesulfonyl-4-O-p-nitrobenzoyl-D-arabino-1,2,3,4-nonanetetrol
  参考文献：
  名称：

  Synthesis of α-S-galactosylceramides with a truncated sphingoid chain

  摘要：

  We present here a convenient synthesis of the truncated sphingoid iodide 15 from D-galactose, in which Mitsunobu reaction was utilized to retrieve successfully an unwanted intermediate, thereby increasing greatly the synthetic efficiency. Subsequent reaction of 15 with the pre-prepared alpha-galactosyl thiol 16 led smoothly to the desired thioglycoside 17 in good yield, from which the catabolically stable thioglycoside analogs of OCH 4 and 22 were synthesized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.103

文献信息

• Synthesis of α-S-galactosylceramides with a truncated sphingoid chain
  作者：Xiangming Zhu、Ravindra T. Dere、Junyan Jiang

  DOI：10.1016/j.tetlet.2011.07.103

  日期：2011.9

  We present here a convenient synthesis of the truncated sphingoid iodide 15 from D-galactose, in which Mitsunobu reaction was utilized to retrieve successfully an unwanted intermediate, thereby increasing greatly the synthetic efficiency. Subsequent reaction of 15 with the pre-prepared alpha-galactosyl thiol 16 led smoothly to the desired thioglycoside 17 in good yield, from which the catabolically stable thioglycoside analogs of OCH 4 and 22 were synthesized. (C) 2011 Elsevier Ltd. All rights reserved.