1,8-bis(1-deoxy-D-lactitol-1-ylamino)-3,6-dioxaoctane

• 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: 1,8-bis(1-deoxy-D-lactitol-1-ylamino)-3,6-dioxaoctane
• 英文别名: (2R,3R,4R,5S)-6-[2-[2-[2-[[(2S,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexyl]amino]ethoxy]ethoxy]ethylamino]-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexane-1,2,4,5-tetrol
• 化学式: C₃₀H₆₀N₂O₂₂
• 分子量: 800.807
• InChiKey: HJTMKLBXUWFESF-KGBJBDOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.4
• 重原子数：
  54
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  403
• 氢给体数：
  18
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  1,8-bis(1-deoxy-D-lactitol-1-ylamino)-3,6-dioxaoctane 、 (Z)-十八碳-9-烯醛 在 溶剂黄146 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 68.0h， 以89%的产率得到
  参考文献：
  名称：

  Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an α,ω-diamino-(oxa)alkyl spacer

  摘要：

  Reduced-sugar based gemini surfactants with an alpha,omega-diamino-(oxa) alkyl spacer exhibit a rich pH-dependent aggregation behavior and are efficient DNA carriers in gene transfection. Herein, we describe an improved synthetic procedure for these amphiphiles. First, a series of novel nonionic bolaform amphiphiles with identical headgroups and alpha,omega-diamino-(oxa) alkyl spacers were synthesized by reductive aminations involving alpha,omega-diaminoalkanes and the appropriate sugars or aldehydes. The bolaform compounds were used as starting materials for the synthesis of the corresponding reduced-sugar based gemini surfactants in a reductive alkylation reaction employing a polymer-bound cyanoborohydride. A series of new gemini surfactants have been synthesized and characterized. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.023
• 作为产物：
  描述：

  1,8-二氨基-3,6-二氧杂辛烷 、 乳糖 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 40.0 ℃ 、900.01 kPa 条件下， 反应 24.0h， 以87%的产率得到1,8-bis(1-deoxy-D-lactitol-1-ylamino)-3,6-dioxaoctane
  参考文献：
  名称：

  Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an α,ω-diamino-(oxa)alkyl spacer

  摘要：

  Reduced-sugar based gemini surfactants with an alpha,omega-diamino-(oxa) alkyl spacer exhibit a rich pH-dependent aggregation behavior and are efficient DNA carriers in gene transfection. Herein, we describe an improved synthetic procedure for these amphiphiles. First, a series of novel nonionic bolaform amphiphiles with identical headgroups and alpha,omega-diamino-(oxa) alkyl spacers were synthesized by reductive aminations involving alpha,omega-diaminoalkanes and the appropriate sugars or aldehydes. The bolaform compounds were used as starting materials for the synthesis of the corresponding reduced-sugar based gemini surfactants in a reductive alkylation reaction employing a polymer-bound cyanoborohydride. A series of new gemini surfactants have been synthesized and characterized. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.023

文献信息

• Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an α,ω-diamino-(oxa)alkyl spacer
  作者：Anno Wagenaar、Jan B.F.N. Engberts

  DOI：10.1016/j.tet.2007.08.023

  日期：2007.10

  Reduced-sugar based gemini surfactants with an alpha,omega-diamino-(oxa) alkyl spacer exhibit a rich pH-dependent aggregation behavior and are efficient DNA carriers in gene transfection. Herein, we describe an improved synthetic procedure for these amphiphiles. First, a series of novel nonionic bolaform amphiphiles with identical headgroups and alpha,omega-diamino-(oxa) alkyl spacers were synthesized by reductive aminations involving alpha,omega-diaminoalkanes and the appropriate sugars or aldehydes. The bolaform compounds were used as starting materials for the synthesis of the corresponding reduced-sugar based gemini surfactants in a reductive alkylation reaction employing a polymer-bound cyanoborohydride. A series of new gemini surfactants have been synthesized and characterized. (C) 2007 Elsevier Ltd. All rights reserved.