[(2R,3R,4R,6S)-3,4-diacetyloxy-6-[(2S,3S,4R)-2-(docosanoylamino)-3,4-bis(phenylmethoxy)octadecoxy]oxan-2-yl]methyl acetate | 412031-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,6S)-3,4-diacetyloxy-6-[(2S,3S,4R)-2-(docosanoylamino)-3,4-bis(phenylmethoxy)octadecoxy]oxan-2-yl]methyl acetate
• CAS: 412031-53-9
• 化学式: C₆₆H₁₀₉NO₁₁
• 分子量: 1092.59
• InChiKey: BZEMNKRGRBJLNQ-KXALZZCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.1
• 重原子数：
  78
• 可旋转键数：
  52
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,6S)-3,4-diacetyloxy-6-[(2S,3S,4R)-2-(docosanoylamino)-3,4-bis(phenylmethoxy)octadecoxy]oxan-2-yl]methyl acetate 在 palladium dihydroxide 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 为溶剂， 40.0 ℃ 、300.0 kPa 条件下， 反应 66.0h， 生成 N-[(2S,3S,4R)-1-[(2S,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxyoctadecan-2-yl]docosanamide
  参考文献：
  名称：

  Immunomodulating glycosphingolipids: an efficient synthesis of a 2′-deoxy-α-galactosyl-GSL

  摘要：

  A new and efficient approach to the total synthesis of 2'-deoxy-alpha-galactosyl glycosphingolipids was accomplished. Commercially available 3,4,6-tri-O-acetylgalactal was used as the chiral starting material for both the sugar and phytosphingosine building blocks required for the synthesis of 1-O-(2-deoxy-alpha-D-galactopyranosyl)-2-docosanoylamino-1,3,4-octadecanetriol. The key step of the synthetic strategy was the stereoselective alpha-glycosidation of the azido precursor of sphingosine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01163-2
• 作为产物：
  描述：

  (2S,3S,4R)-2-azido-3,4-bis(benzyloxy)octadecan-1-ol 在 吡啶 、 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 三苯基氢化锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 38.5h， 生成 [(2R,3R,4R,6S)-3,4-diacetyloxy-6-[(2S,3S,4R)-2-(docosanoylamino)-3,4-bis(phenylmethoxy)octadecoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Immunomodulating glycosphingolipids: an efficient synthesis of a 2′-deoxy-α-galactosyl-GSL

  摘要：

  A new and efficient approach to the total synthesis of 2'-deoxy-alpha-galactosyl glycosphingolipids was accomplished. Commercially available 3,4,6-tri-O-acetylgalactal was used as the chiral starting material for both the sugar and phytosphingosine building blocks required for the synthesis of 1-O-(2-deoxy-alpha-D-galactopyranosyl)-2-docosanoylamino-1,3,4-octadecanetriol. The key step of the synthetic strategy was the stereoselective alpha-glycosidation of the azido precursor of sphingosine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01163-2