6-O-dodecyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 66854-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-O-dodecyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: (1S,2R,6R,8R,9S)-8-(dodecoxymethyl)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 66854-09-9
• 化学式: C₂₄H₄₄O₆
• 分子量: 428.61
• InChiKey: WHLBCNRCXJZXMF-CDJZJNNCSA-N

物化性质

• 沸点：
  483.0±40.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-O-dodecyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.5h， 以95%的产率得到(2S,3R,4S,5S,6R)-6-(1-hydroxytridecyl)oxane-2,3,4,5-tetrol
  参考文献：
  名称：

  半乳糖和氨基葡萄糖两亲肟的有效合成

  摘要：

  已合成并表征了半乳糖和葡糖胺的新型两亲肟。肟官能团已被引入非离子表面活性剂的第一和第六位置，该非离子表面活性剂由糖极性头和亲脂性侧链组成。该化合物可溶于吡啶，微溶于其他极性有机溶剂和水。

  DOI：

  10.1016/j.tetlet.2012.02.086
• 作为产物：
  描述：

  alpha-D-半乳糖 在 硫酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-O-dodecyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis, surface tension properties and antibacterial activities of amphiphilic d -galactopyranose derivatives

  摘要：

  Several amphiphilic D-galactopyranose derivatives were synthesized in which the glycosidic moiety was separated from the hydrophobic alkyl chain (along 8 or 12 carbon atoms) by a spacer arm (butyl, butynyl or benzyl) in order to increase their surfactant properties and to obtain new antibacterial compounds. The surface tensions of the products were analyzed by Critical Micelle Concentration (CMC) and gamma(CMC) measurements and the antimicrobial activities were assayed against 10 bacterial species by Minimum Inhibitory Concentration (MIC) determination in liquid broth. The introduction of an aliphatic spacer arm increased the amphiphilic properties of the compounds and the CMC values were 40-500 times lower than their analogs without spacer arm. In the same manner, the spacer arms significantly increased the antibacterial power of the compounds. The products 4d and 4e exhibiting a C12 alkyl chain and an aliphatic spacer arm (butyl and butynyl) were the best surfactants (CMC = 0.023 and 0.032 mmol/L, respectively) and presented also the best antibacterial activities (MIC = 15.62 and 3.91 mu g/mL for Micrococcus luteus, respectively). But the antibacterial activity of the newly synthesized products seemed to depend more on the cell wall composition of the bacteria than only on the amphiphilic character of the compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.032

文献信息

• Gosenca, Mirjam; Mravljak, Janez; Gasperlin, Mirjana, Acta Chimica Slovenica, 2013, vol. 60, # 2, p. 310 - 322
  作者：Gosenca, Mirjam、Mravljak, Janez、Gasperlin, Mirjana、Obreza, Ales

  DOI：——

  日期：——
• Synthese tensioaktiver 3-O-Alkyl-α-d-glucopyranosyl-fluoride und 6-O-Alkyl-α-d-galactopyranosylfluoride
  作者：Ralf Miethchen、Torsten Gabriel、Dietmar Peters、Jens Holz、Manfred Michalik

  DOI：10.1016/0008-6215(91)80040-t

  日期：1991.7
• Urata, Kouichi; Yano, Shinji; Takaishi, Naotake, Journal of the American Oil Chemists' Society, 1995, vol. 72, # 1, p. 73 - 82
  作者：Urata, Kouichi、Yano, Shinji、Takaishi, Naotake

  DOI：——

  日期：——
• Organofluorine compounds and fluorinating agents. 14. Thermotropic Liquid-Crystalline Glycosyl Fluorides
  作者：Ralf Miethchen、Cornelia Zur

  DOI：10.1002/prac.19953370142

  日期：——

  The liquid crystalline 6-O-alkyl-alpha-D-galactopyranosyl fluorides (3a-f) and the mesogenic 6-O-dodecyl-alpha-D-glucopyranosyl fluoride (7) were prepared from the homologous 6-O-alkyl-1,2:3,4-di-O-isopropylidene-alpha-D-galacto-pyranosides (1a-f) and from the methyl 2,3,4-tri-O-benzyl-glucopyranoside (4), respectively, in two and three steps. The fluorinations of 1a-f to the alpha-fluorides 2a-f and of 5 to the alpha-fluoride 6 were carried out with the reagent system HF/nitromethane/acetic anhydride, which simultaneously effects the complete exchange of the isopropylidene groups (1a-f) and of the benzyl groups (5) for acetyl functions in the non-glycosidic positions. Moreover, the 6-O-dodecyl-2,3,4-tri-O-acetyl-beta-D-galactopyranosyl fluoride (11) was prepared in three steps from the 6-O-dodecyl-galactopyranose (8). The stereoselective introduction of the fluoride into the beta-anomeric position (10 --> 11) was achieved by bromide-fluoride exchange with the two-phase system triethylamine-trishydrofluoride/petroleum ether. Dodecyl 6-deoxy-6-fluoro-alpha-D-glucopyranoside (13), prepared from the glucoside 12 with the fluorinating agent DAST, shows a narrow monotropic SA-phase and lyotropic liquid crystalline behaviour in contact with water. Dodecyl 6-deoxy-6-fluoro-beta-D-galactopyranoside (17), prepared in three steps from the acetal 14, does not form mesophases. The liquid crystalline behaviour of the amphiphilic glycosyl fluorides 3a-f, 7, and of the 6-deoxy-6-fluoro derivative 13 is described.
• MIETHCHEN, RALF;GABRIEL, TORSTEN;PETERS, DIETMAR;HOLZ, JENS;MICHALIK, MAN+, CARBOHYDR. RES., 214,(1991) N, C. 331-336
  作者：MIETHCHEN, RALF、GABRIEL, TORSTEN、PETERS, DIETMAR、HOLZ, JENS、MICHALIK, MAN+

  DOI：——

  日期：——