2-hexacosanoylamino-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol | 1333920-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hexacosanoylamino-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol
• CAS: 1333920-15-2
• 化学式: C₆₅H₁₀₃NO₈S
• 分子量: 1058.6
• InChiKey: HFCYXRABCYDCRS-VERGDKKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.16
• 重原子数：
  75.0
• 可旋转键数：
  43.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  104.71
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-hexacosanoylamino-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以72%的产率得到2-hexacosanoylamino-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol
  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-azido-1-iodo-3,4-O-isopropylidene-D-ribo-3,4-nonanediol 在 四丁基硫酸氢铵 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 47.0h， 生成 2-hexacosanoylamino-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol
  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