1,6-bis(1-deoxy-D-glucitol-1-ylamino)hexane | 199680-37-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-bis(1-deoxy-D-glucitol-1-ylamino)hexane
• 英文别名: (2R,3R,4R,5S)-6-[6-[[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]hexylamino]hexane-1,2,3,4,5-pentol
• CAS: 199680-37-0
• 化学式: C₁₈H₄₀N₂O₁₀
• 分子量: 444.523
• InChiKey: HCVSYGHISGTMMH-OVSMWIARSA-N

物化性质

• 沸点：
  792.9±60.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.5
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  226
• 氢给体数：
  12
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (Z)-十八碳-9-烯醛 、 1,6-bis(1-deoxy-D-glucitol-1-ylamino)hexane 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78%的产率得到(2R,3R,4R,5S)-6-(((Z)-Octadec-9-enyl)-{6-[((Z)-octadec-9-enyl)-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxy-hexyl)-amino]-hexyl}-amino)-hexane-1,2,3,4,5-pentaol
  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：

  1,6-己二胺 、 葡萄糖 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 40.0 ℃ 、4.0 MPa 条件下， 反应 24.0h， 生成 1,6-bis(1-deoxy-D-glucitol-1-ylamino)hexane
  参考文献：
  名称：

  A synthetic strategy for novel nonsymmetrical bola amphiphiles based on carbohydrates

  摘要：

  A number of novel nonionic bolaform amphiphiles with nonidentical aldityl head groups, 1-(1-deoxy-D-galactitol-l-ylamino)-6-(1-deoxy-D- galactitol-1-ylamino)hexane (4a), 1-(1-deoxy-D-mannitol-1-ylamino)-6-(1-deoxy-D-glucitol-1-ylamino)hexane (4b). and 1-(1-deoxy-D-tialactitol-1-ylamino)-6-(1-deoxy-D-Mannitol-1-ylamino)hexane (4c) were synthesized by two successive reductive aminations involving 1,6-diaminohexane (4) and the appropriate (1)-aldohexoses (D-glucose, D-mannose, and D-galactose) using 5% Pd on carbon as the catalyst. Typical reaction conditions were 40 degreesC, 4 MPa hydrogen and a reaction time of 4.5 h. The compounds were isolated as white solids in yields ranging from 39% to 72%. The intermediate aminoalditols,1-(1-deoxy-D-glucitol- 1-ylamino)-6-aminohexane (3a) and 1-(1-deoxy-D-galactitol-1-ylamino)-6-aminohexane (3b) were obtained as off-white solids in 80-85% yield. The bolaform amphiphiles containing 1-deoxy-D-glucitol head group(s) showed markedly lower melting points than the compounds with the 1-deoxy-D-mannitol and 1-deoxy-D-galactitol head groups, due to the presence of 1,3-syn interactions within the carbohydrate moiety. The novel bolaform compounds are potential starting materials for the synthesis of a broad range of gemini surfactants with nonidentical, carbohydrate-based head groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.01.021

文献信息

• A synthetic strategy for novel nonsymmetrical bola amphiphiles based on carbohydrates
  作者：Boelo Schuur、Anno Wagenaar、André Heeres、Erik H.J. Heeres

  DOI：10.1016/j.carres.2004.01.021

  日期：2004.4

  A number of novel nonionic bolaform amphiphiles with nonidentical aldityl head groups, 1-(1-deoxy-D-galactitol-l-ylamino)-6-(1-deoxy-D- galactitol-1-ylamino)hexane (4a), 1-(1-deoxy-D-mannitol-1-ylamino)-6-(1-deoxy-D-glucitol-1-ylamino)hexane (4b). and 1-(1-deoxy-D-tialactitol-1-ylamino)-6-(1-deoxy-D-Mannitol-1-ylamino)hexane (4c) were synthesized by two successive reductive aminations involving 1,6-diaminohexane (4) and the appropriate (1)-aldohexoses (D-glucose, D-mannose, and D-galactose) using 5% Pd on carbon as the catalyst. Typical reaction conditions were 40 degreesC, 4 MPa hydrogen and a reaction time of 4.5 h. The compounds were isolated as white solids in yields ranging from 39% to 72%. The intermediate aminoalditols,1-(1-deoxy-D-glucitol- 1-ylamino)-6-aminohexane (3a) and 1-(1-deoxy-D-galactitol-1-ylamino)-6-aminohexane (3b) were obtained as off-white solids in 80-85% yield. The bolaform amphiphiles containing 1-deoxy-D-glucitol head group(s) showed markedly lower melting points than the compounds with the 1-deoxy-D-mannitol and 1-deoxy-D-galactitol head groups, due to the presence of 1,3-syn interactions within the carbohydrate moiety. The novel bolaform compounds are potential starting materials for the synthesis of a broad range of gemini surfactants with nonidentical, carbohydrate-based head groups. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.