Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester | 848827-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS: 848827-63-4
• 化学式: C₄₄H₆₅N₃O₁₀
• 分子量: 796.014
• InChiKey: CNNXEJDROKHIRJ-JUPBTETLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.48
• 重原子数：
  57.0
• 可旋转键数：
  28.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  164.58
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester 在 吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三苯基膦 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

  摘要：

  Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive D-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6OH underwent glycosylation in excellent alpha-anomeric selectivity. A variety of alpha-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides alpha-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-gamma and IL-4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.027
• 作为产物：
  描述：

  3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,2,3,4-tetraol 在 吡啶 、 2,6-二甲基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium hydride 、 溶剂黄146 、 tetramethylguanidinum azide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

  摘要：

  Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive D-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6OH underwent glycosylation in excellent alpha-anomeric selectivity. A variety of alpha-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides alpha-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-gamma and IL-4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.027