[(2R,3S,4S,5R,6S)-3-benzoyloxy-6-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-prop-2-enoxypropoxy]-4,5-bis(phenylmethoxy)oxan-2-yl]methyl benzoate | 492461-18-4

• 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: [(2R,3S,4S,5R,6S)-3-benzoyloxy-6-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-prop-2-enoxypropoxy]-4,5-bis(phenylmethoxy)oxan-2-yl]methyl benzoate
• CAS: 492461-18-4
• 化学式: C₅₅H₅₁NO₁₂
• 分子量: 918.009
• InChiKey: ATYJRQFGFXXAQY-MLHVCIOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  68
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-3-benzoyloxy-6-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-prop-2-enoxypropoxy]-4,5-bis(phenylmethoxy)oxan-2-yl]methyl benzoate 在 四(三苯基膦)钯 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1-羟基苯并三唑一水物 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 (2R,3S,4S,5R,6S)-6-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-oxo-3-(tetradecylamino)propoxy)-2-((benzoyloxy)methyl)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-3-yl benzoate
  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：

  C₃₄H₃₂O₈ 在 四氮唑 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(2R,3S,4S,5R,6S)-3-benzoyloxy-6-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-prop-2-enoxypropoxy]-4,5-bis(phenylmethoxy)oxan-2-yl]methyl benzoate
  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

文献信息

• A convenient and highly stereoselective approach for α-galactosylation performed by galactopyranosyl dibenzyl phosphite with remote participating groups
  作者：Yu-Pei Cheng、Hui-Ting Chen、Chun-Cheng Lin

  DOI：10.1016/s0040-4039(02)01849-x

  日期：2002.10

  By using 4- and 6-acyl remote group participation, a galactosyl phosphite donor exhibits exceptionally high alpha-anomeric selectivity for primary and secondary hydroxyl acceptors. It was observed that temperature played an important factor in glycosylation. The higher alpha-selectivities were obtained at higher reaction temperatures. (C) 2002 Elsevier Science Ltd. All rights reserved.