2-azido-3,4-O-isopropylidene-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-[N-(5-dimethylaminonaphth-1-ylsulfonyl)amido]-α-D-galactopyranosyl)-D-ribo-octadecane-1,3,4-triol | 1309598-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-azido-3,4-O-isopropylidene-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-[N-(5-dimethylaminonaphth-1-ylsulfonyl)amido]-α-D-galactopyranosyl)-D-ribo-octadecane-1,3,4-triol
• 英文别名: N-[[(2R,3S,4S,5R,6S)-6-[(2S)-2-azido-2-[(4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl]ethoxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 1309598-26-2
• 化学式: C₆₀H₈₁N₅O₉S
• 分子量: 1048.4
• InChiKey: FNMJIENAIBMKJR-RSOBOXAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  75
• 可旋转键数：
  32
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-azido-3,4-O-isopropylidene-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-[N-(5-dimethylaminonaphth-1-ylsulfonyl)amido]-α-D-galactopyranosyl)-D-ribo-octadecane-1,3,4-triol 在 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.0h， 生成
  参考文献：
  名称：

  An improved synthesis of dansylated α-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells

  摘要：

  A highly efficient synthesis of the biologically important fluorescent probe dansyl alpha-GalCer is presented. Key in our strategy is the incorporation of the fluorescent dansyl group at an early stage in the synthesis to facilitate in the monitoring and purification of intermediates via TLC and flash column chromatography, respectively, and the use of a high yielding alpha-selective glycosylation reaction between the phytosphingosine lipid and a galactosyl iodide donor. The ability of dansyl alpha-GalCer to activate iNKT cells and to serve as a fluorescent marker for the uptake of glycolipid by dendritic cells is also presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.014
• 作为产物：
  描述：

  1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-6-[N-(5-dimethylaminonaphth-1-ylsulfonyl)acetamido]-α-D-galactopyranoside 在 甲醇 、 碘代三甲硅烷 、 sodium methylate 、 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 93.25h， 生成 2-azido-3,4-O-isopropylidene-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-[N-(5-dimethylaminonaphth-1-ylsulfonyl)amido]-α-D-galactopyranosyl)-D-ribo-octadecane-1,3,4-triol
  参考文献：
  名称：

  An improved synthesis of dansylated α-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells

  摘要：

  A highly efficient synthesis of the biologically important fluorescent probe dansyl alpha-GalCer is presented. Key in our strategy is the incorporation of the fluorescent dansyl group at an early stage in the synthesis to facilitate in the monitoring and purification of intermediates via TLC and flash column chromatography, respectively, and the use of a high yielding alpha-selective glycosylation reaction between the phytosphingosine lipid and a galactosyl iodide donor. The ability of dansyl alpha-GalCer to activate iNKT cells and to serve as a fluorescent marker for the uptake of glycolipid by dendritic cells is also presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.014

文献信息

• An improved synthesis of dansylated α-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells
  作者：Janice M.H. Cheng、Stephanie H. Chee、Deborah A. Knight、Hans Acha-Orbea、Ian F. Hermans、Mattie S.M. Timmer、Bridget L. Stocker

  DOI：10.1016/j.carres.2011.02.014

  日期：2011.5

  A highly efficient synthesis of the biologically important fluorescent probe dansyl alpha-GalCer is presented. Key in our strategy is the incorporation of the fluorescent dansyl group at an early stage in the synthesis to facilitate in the monitoring and purification of intermediates via TLC and flash column chromatography, respectively, and the use of a high yielding alpha-selective glycosylation reaction between the phytosphingosine lipid and a galactosyl iodide donor. The ability of dansyl alpha-GalCer to activate iNKT cells and to serve as a fluorescent marker for the uptake of glycolipid by dendritic cells is also presented. (C) 2011 Elsevier Ltd. All rights reserved.