(2S,3S,4R,2'R)-1-O-(2''-acetamido-3'',4'',6''-tri-O-acetyl-2''-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-2-(2'-acetoxyhexadecanoyl)aminooctadecane-1,3,4-triol | 220869-83-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3S,4R,2'R)-1-O-(2''-acetamido-3'',4'',6''-tri-O-acetyl-2''-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-2-(2'-acetoxyhexadecanoyl)aminooctadecane-1,3,4-triol
• CAS: 220869-83-0
• 化学式: C₅₇H₉₄N₂O₁₅
• 分子量: 1047.38
• InChiKey: DPAWFCLUVYLQCN-CVYQLIPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.84
• 重原子数：
  74.0
• 可旋转键数：
  41.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  228.39
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,2'R)-1-O-(2''-acetamido-3'',4'',6''-tri-O-acetyl-2''-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-2-(2'-acetoxyhexadecanoyl)aminooctadecane-1,3,4-triol 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到(2S,3S,4R,2'R)-1-O-(2''-acetamido-2''-deoxy-β-D-glucopyranosyl)-2-(2'-hydroxyhexadecanoyl)aminooctadecane-1,3,4-triol
  参考文献：
  名称：

  Stereocontrolled synthesis of novel phytosphingosine-type glucosaminocerebrosides

  摘要：

  D-ribo-Phytosphingosine 1 was conveniently synthesized from N-benzoyl-D-glucosamine 3 by an improved route in which regioselective O-methanesulfonation and diastereoselective Grignard addition are involved as key steps. Using a synthetic intermediate of 1, novel D-ribo-phytosphingosinetype glycolipids 2a and 2b, unnatural homologues of antifungal cerebrosides Halicylindrosides, were efficiently synthesized in a stereocontrolled manner. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01104-1
• 作为产物：
  描述：

  (4R,5R)-4-[(4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-2-methyl-[1,3]dioxan-5-ol 在 盐酸 、 sodium periodate 、 4 A molecular sieve 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 、 四氯化钛 、 苯硫酚 、 N,N-二异丙基乙胺 、 n-tetradecylmagnesium chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (2S,3S,4R,2'R)-1-O-(2''-acetamido-3'',4'',6''-tri-O-acetyl-2''-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-2-(2'-acetoxyhexadecanoyl)aminooctadecane-1,3,4-triol
  参考文献：
  名称：

  Stereocontrolled synthesis of novel phytosphingosine-type glucosaminocerebrosides

  摘要：

  D-ribo-Phytosphingosine 1 was conveniently synthesized from N-benzoyl-D-glucosamine 3 by an improved route in which regioselective O-methanesulfonation and diastereoselective Grignard addition are involved as key steps. Using a synthetic intermediate of 1, novel D-ribo-phytosphingosinetype glycolipids 2a and 2b, unnatural homologues of antifungal cerebrosides Halicylindrosides, were efficiently synthesized in a stereocontrolled manner. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01104-1