(S)-3-((2R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-pentadecanoylamino-propionic acid methyl ester | 848827-49-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-((2R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-pentadecanoylamino-propionic acid methyl ester
• CAS: 848827-49-6
• 化学式: C₄₆H₆₃NO₉
• 分子量: 774.008
• InChiKey: IIGWGIYQEVNKBN-AUTDLCMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.76
• 重原子数：
  56.0
• 可旋转键数：
  25.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  110.78
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((2R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-pentadecanoylamino-propionic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 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：

  methyl (2S)-3-hydroxy-2-(pentadecanoylamino)propanoate 、 2,3-双-O-(苯基甲基)-4,6-O-[(R)-苯基亚甲基]-1-硫代-B-D-吡喃葡萄糖苷苯酯 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 生成 、 (S)-3-((2R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-pentadecanoylamino-propionic acid methyl 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