((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-triisopropyl-silane | 412031-50-6

• 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: ((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-triisopropyl-silane
• 英文别名: [(2S,3S,4R)-2-azido-3,4-bis(phenylmethoxy)octadecoxy]-tri(propan-2-yl)silane
• CAS: 412031-50-6
• 化学式: C₄₁H₆₉N₃O₃Si
• 分子量: 680.103
• InChiKey: DBEKHOOOYKLJBD-HMVVSKLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.12
• 重原子数：
  48
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-triisopropyl-silane 在 吡啶 、 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 三苯基氢化锡 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 40.17h， 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
• 作为产物：
  描述：

  Trifluoro-methanesulfonic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-triisopropylsilanyloxymethyl-heptadecyl ester 在 sodium azide 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以1.04 g的产率得到((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-triisopropyl-silane
  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