(2S,3S)-3-azidoheptadecane-1,2-diol | 176966-69-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2S,3S)-3-azidoheptadecane-1,2-diol
• CAS: 176966-69-1
• 化学式: C₁₇H₃₅N₃O₂
• 分子量: 313.484
• InChiKey: KRIKHZWUPQQPND-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  22.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  89.22
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-azidoheptadecane-1,2-diol 在 palladium dihydroxide potassium permanganate 、 sodium periodate 、 氢气 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 为溶剂， 生成 (2S)-2-t-butoxycarbonylamino-hexadecanoic acid
  参考文献：
  名称：

  A general approach to the enantiomeric synthesis of lipidic α-amino acids, peptides and vicinal amino alcohols

  摘要：

  A general methodology for the synthesis of saturated lipidic amino acids based on the oxidative cleavage of amino diols obtained by the regioselective opening of enantiomerically enriched 2,3-epoxy alcohols is described. The method opens the way to the synthesis of the enantiomers of lipidic 2-amino alcohols and home- and hetero-peptides. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00084-5
• 作为产物：
  描述：

  [(2R,3R)-3-tetradecyloxiran-2-yl]methanol 在 sodium azide 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 生成 (2S,3S)-3-azidoheptadecane-1,2-diol
  参考文献：
  名称：

  Synthesis, in vitro cytotoxicity and in vivo anti-inflammatory activity of long chain 3-amino-1,2-diols

  摘要：

  The synthesis of long chain 3-amino-1,2-diols was carried out based on Sharpless asymmetric epoxidation of long chain allylic alcohols and regioselective nucleophilic ring opening by azido group. The in vitro cytotoxicity of the compounds prepared was evaluated against six solid tumor cell lines (A2780, H322, LL, WiDr, C26-10, UMSCC-22B). Free 3-amino-1,2-diols exhibited IC50 values between 1.45 mu M and 32 mu M. These compound!; also presented interesting inhibition of carrageenin-induced paw edema in rats (85.3% 79.6% at a concentration of 0.15 mmol/kg). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00084-0

文献信息

• A general approach to the enantiomeric synthesis of lipidic α-amino acids, peptides and vicinal amino alcohols
  作者：George Kokotos、JoséM. Padrón、Caterina Noula、William A. Gibbons、Victor S. Martín

  DOI：10.1016/0957-4166(96)00084-5

  日期：1996.3

  A general methodology for the synthesis of saturated lipidic amino acids based on the oxidative cleavage of amino diols obtained by the regioselective opening of enantiomerically enriched 2,3-epoxy alcohols is described. The method opens the way to the synthesis of the enantiomers of lipidic 2-amino alcohols and home- and hetero-peptides. (C) 1996 Elsevier Science Ltd
• Synthesis, in vitro cytotoxicity and in vivo anti-inflammatory activity of long chain 3-amino-1,2-diols
  作者：JoséM. Padrón、Victor S. Martin、Dimitra Hadjipavlou-Litina、Caterina Noula、Violetta Constantinou-Kokotou、Godefridus J. Peters、George Kokotos

  DOI：10.1016/s0960-894x(99)00084-0

  日期：1999.3

  The synthesis of long chain 3-amino-1,2-diols was carried out based on Sharpless asymmetric epoxidation of long chain allylic alcohols and regioselective nucleophilic ring opening by azido group. The in vitro cytotoxicity of the compounds prepared was evaluated against six solid tumor cell lines (A2780, H322, LL, WiDr, C26-10, UMSCC-22B). Free 3-amino-1,2-diols exhibited IC50 values between 1.45 mu M and 32 mu M. These compound!; also presented interesting inhibition of carrageenin-induced paw edema in rats (85.3% 79.6% at a concentration of 0.15 mmol/kg). (C) 1999 Elsevier Science Ltd. All rights reserved.