(1R,4'S,5'S)-1-<4'-(3'',4'',6''-tri-O-acetyl-2''-chloroacetamido-2''-deoxy-β-D-glucopyranosyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol | 220869-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4'S,5'S)-1-<4'-(3'',4'',6''-tri-O-acetyl-2''-chloroacetamido-2''-deoxy-β-D-glucopyranosyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol
• CAS: 220869-77-2
• 化学式: C₃₉H₅₉ClN₂O₁₁
• 分子量: 767.357
• InChiKey: JXRLLAXOBGIGNC-QSNLUTIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  53.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  168.28
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (1R,4'S,5'S)-1-<4'-(3'',4'',6''-tri-O-acetyl-2''-chloroacetamido-2''-deoxy-β-D-glucopyranosyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol 在 盐酸 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.5h， 生成 (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：

  (1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol 在 4 A molecular sieve 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 生成 (1R,4'S,5'S)-1-<4'-(3'',4'',6''-tri-O-acetyl-2''-chloroacetamido-2''-deoxy-β-D-glucopyranosyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol
  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