{2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium | 221697-44-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium
• 英文别名: 2-[[(2S)-2-azido-3-[2-cyanoethoxy-[[(2R,3R,4S,5R,6S)-6-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]phosphoryl]oxypropoxy]-(2-cyanoethoxy)phosphoryl]oxyethyl-trimethylazanium
• CAS: 221697-44-5
• 化学式: C₄₇H₆₅N₆O₁₅P₂
• 分子量: 1016.01
• InChiKey: IVEAKJNABPATFO-MZHQLZFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  70
• 可旋转键数：
  32
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  216
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 (S)-GGPL-III
  参考文献：
  名称：

  Synthesis and absolute configuration of a novel aminoglycoglycerolipid, species-specific major immunodeterminant of Mycoplasma fermentans

  摘要：

  In order to determine the absolute configuration of a novel aminoglycoglycerolipid isolated from Mycoplasma fermentans, the possible two diastereomers were stereoselectively synthesized by using (S)- and (R)-glycidols as the key building block. Their H-1-H-1-cosy spectra compared with those of the natural product allowed us to determine the absolute configuration of the glycolipid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00191-4
• 作为产物：
  描述：

  3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-L-glycerol 在 四氮唑 、 silver(II) bis(pyridine-2,6-dicarboxylate) 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium
  参考文献：
  名称：

  Synthesis and absolute configuration of a novel aminoglycoglycerolipid, species-specific major immunodeterminant of Mycoplasma fermentans

  摘要：

  In order to determine the absolute configuration of a novel aminoglycoglycerolipid isolated from Mycoplasma fermentans, the possible two diastereomers were stereoselectively synthesized by using (S)- and (R)-glycidols as the key building block. Their H-1-H-1-cosy spectra compared with those of the natural product allowed us to determine the absolute configuration of the glycolipid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00191-4

文献信息

• Synthesis and absolute configuration of a novel aminoglycoglycerolipid, species-specific major immunodeterminant of Mycoplasma fermentans
  作者：Yoshihiro Nishida、Yusuke Takamori、Hiroshi Ohrui、Ineo Ishizuka、Kazuhiro Matsuda、Kazukiyo Kobayashi

  DOI：10.1016/s0040-4039(99)00191-4

  日期：1999.3

  In order to determine the absolute configuration of a novel aminoglycoglycerolipid isolated from Mycoplasma fermentans, the possible two diastereomers were stereoselectively synthesized by using (S)- and (R)-glycidols as the key building block. Their H-1-H-1-cosy spectra compared with those of the natural product allowed us to determine the absolute configuration of the glycolipid. (C) 1999 Elsevier Science Ltd. All rights reserved.