2-azido-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol | 1333920-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol
• 英文别名: [(2R,3S,4S,5R,6R)-6-[(2R)-2-azido-2-[(4S,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl]ethyl]sulfanyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 1333920-11-8
• 化学式: C₃₉H₅₁N₃O₇S
• 分子量: 705.916
• InChiKey: WFZZTSOATZIQBY-RJBSGGITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-azido-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol 在 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 为溶剂， 反应 23.0h， 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
• 作为产物：
  描述：

  (2R,3S,4R)-1,3-O-benzylidene-1,2,3,4-nonanetetrol 在 吡啶 、 sodium azide 、 四丁基硫酸氢铵 、 碳酸氢钠 、 对甲苯磺酸 、 lithium iodide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 125.0h， 生成 2-azido-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

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.