hexyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside | 85618-25-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: hexyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: hexyl 2,3,4,6-tetra-O-acetyl-β-D-thioglucopyranoside；2-(Acetoxymethyl) Hexyl beta-D-Thioglucopyranoside Triacetate；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-hexylsulfanyloxan-2-yl]methyl acetate
• CAS: 85618-25-3
• 化学式: C₂₀H₃₂O₉S
• 分子量: 448.535
• InChiKey: KXJGUZALRMDGTN-OBKDMQGPSA-N

物化性质

• 沸点：
  502.4±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  hexyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 过氧化脲素 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以87%的产率得到1-deoxy-1-[(R/S)-(n-hexyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  尿素-过氧化氢促使硫代糖苷选择性和受控地氧化为亚砜和砜。

  摘要：

  已经报道了使用脲-过氧化氢（UHP）将硫代糖苷选择性和控制地氧化为相应的糖基亚砜和砜的实用方法。在60°C下使用1.5当量的UHP选择性地获得了广泛的糖基亚砜，而在80°C下使用2.5当量的UHP在乙酸中实现了相应的砜。显着地，发现在硫化物的氧化过程中对氧化敏感的烯烃官能团是稳定的。

  DOI：

  10.3762/bjoc.13.113
• 作为产物：
  描述：

  α-D(+)-五乙酰葡萄糖 在 磷化氢 、 氢溴酸 、 溴 、 potassium carbonate 、 sodium hydrogensulfite 作用下， 以 水 、 乙酸酐 、 丙酮 为溶剂， 反应 1.5h， 生成 hexyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Saito, Setsuo; Tsuchiya, Tomofusa, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 2, p. 503 - 508

  摘要：

  DOI：

文献信息

• Synthesis and surface properties of alkyl β‑ ‑thioglucopyranoside
  作者：Xiubing Wu、Langqiu Chen、Fang Fu、Yulin Fan、Zhiqiang Luo

  DOI：10.1016/j.molliq.2018.11.134

  日期：2019.2

  Alkyl thioglycosides are a class of nonionic sugar-based sulfur-containing surfactants and bioreagents. The surfactants 1,2‑trans alkyl β‑d‑thioglucopyranosides with different alkyl chain length (n = 6–12) were stereoselectively prepared by the Helferich method. Their properties including HLB number, logP value, water solubility, foam property, emulsifying property, surface property and thermotropic

  烷基硫糖苷是一类非离子的基于糖的含硫表面活性剂和生物试剂。用Helferich方法立体选择性地制备了具有不同烷基链长（n = 6-12）的表面活性剂1,2-反烷基β - d-硫代吡喃葡萄糖苷。主要研究了它们的性质，包括HLB值，log P值，水溶性，泡沫性质，乳化性质，表面性质和热致液晶性质。结果表明，随着烷基链长的增加，log B值增加，其HLB值和水溶性降低。烷基β - d-硫葡糖苷已经不溶于n≥10的水中。在临界胶束浓度（CMC）时，两种β - d-硫代吡喃葡萄糖苷（n = 8、9）都将相关水溶液的表面张力降低至近29 mN·m -1。，它们还具有优异的起泡能力和泡沫稳定性。壬基β - d-硫代吡喃葡萄糖苷对正辛烷/水系统和甲苯/水系统均具有良好的乳化性能。观察到烷基β - d-硫代吡喃葡萄糖苷（n = 6-12）具有热致液晶特性。
• A Sugar-Based Gelator for Marine Oil-Spill Recovery
  作者：Amol M. Vibhute、Venkatanarayana Muvvala、Kana M. Sureshan

  DOI：10.1002/anie.201510308

  日期：2016.6.27

  easy‐to‐make glucose‐derived PSOGs that disperse in the oil phase uniformly when applied as a fine powder. These gelators were shown to selectively congeal many oils, including crude oil, from oil–water mixtures to form stable gels, which is an essential property for efficient oil‐spill recovery. We have demonstrated that these PSOGs can be applied aerially as a solid powder onto a mixture of crude oil

  海上溢油构成环境灾难，对经济和生态系统造成严重不利影响。相选择性有机胶凝剂（PSOG）是可以从油水混合物中选择性凝结油的分子，已被认为可用于溢油回收。但是，主要缺点在于将PSOG应用于散布在大面积区域的溢油的方式。由于各种原因，所提出的使用载体溶剂的方法是不切实际的。尽管将PSOG直接用作固体是理想的，但尚不清楚，这可能是由于固体在油中的分散性较差所致。我们设计了五种便宜且易于制造的葡萄糖衍生的PSOG，它们以细粉形式均匀分散在油相中。这些胶凝剂可选择性凝结许多油，包括原油，从油水混合物形成稳定的凝胶，这是有效溢油回收的一项基本特性。我们已经证明，这些PSOG可以以固体粉末形式空中应用到原油和海水的混合物中，然后可以将凝结的油sc出。我们创新的应用模式和PSOG的低成本为漏油回收提供了实用的解决方案。
• Synthesis and liquid crystalline properties of the n-alkyl 1-thio-α-d-glucopyranosides, a new homologous series of carbohydrate mesogens
  作者：Henk A. van Doren、Ralph van der Geest、Richard M. Kellogg、Hans Wynberg

  DOI：10.1016/0008-6215(89)85007-4

  日期：1989.12

  deacetylation. The n -propyl and n -butyl derivatives are not thermotropic, the n -pentyl derivative is monotropic, and the compounds with n -hexyl and longer alkyl chains are enantiotropic, the largest liquid crystalline range being from ±100–175° for the n -undecyl derivative. The transition point data are typical for smectic behavior, and X-ray data and texture observations are indicative of a smectic A d phase

  摘要用1,2,3,4,6-五戊-O-乙酰基-β-d-吡喃葡萄糖处理1,2,3,4,6-戊-O-乙酰基-β-d-吡喃葡萄糖制备了n-烷基1-硫代-α-d-吡喃葡萄糖苷（正丙基至正十二烷基）。在三氟化硼醚化物的存在下链烷硫醇，然后脱乙酰化。正丙基和正丁基衍生物不是热致性的，正戊基衍生物是单亲的，具有正己基和较长烷基链的化合物是对映体的，n的最大液晶范围为±100–175° -十一烷基衍生物。转变点数据是近晶行为的典型特征，X射线数据和纹理观察表明近晶A d相。
• Non-Amphiphilic Carbohydrate Liquid Crystals Containing an Intact Monosaccharide Moiety
  作者：E. Smits、J. B.F.N. Engberts、R. M. Kellogg、H. A. Van Doren

  DOI：10.1080/10587259508038691

  日期：1995.2

  A chiral rigid moiety which forms the basis of a new class of non-amphiphilic carbohydrate liquid crystals has been developed. This moiety contains a fully intact glucopyranose ring embedded in a trans-decalin structure. The original carbohydrate is substituted so that only two hydroxyl groups are left, resulting in derivatives with reduced hydrophilicity. The substituents R and X-R' on the 4,6-O-ylidene beta-D-glucopyranoside are in the equatorial position and can be varied extensively, using straightforward synthetic procedures. Investigations as to the requirements for R and X-R' for inducing liquid-crystalline behavior have shown that at least one of the substituents should contain a large, polarizable aromatic moiety. An aromatic Schiff base fulfils this requirement.
• Synthesis, purification and liquid-crystalline behaviour of several alkyl 1-thio-d-glycopyranosides
  作者：Saskia A. Galema、Jan B.F.N. Engberts、Henk A. van Doren

  DOI：10.1016/s0008-6215(97)00185-7

  日期：1997.10

  This paper describes the synthesis, purification, and liquid-crystalline behaviour of a series of alkyl 1-thioglycopyranosides. The synthesis of these derivatives was carried out via a Lewis acid mediated coupling of the fully acetylated monosaccharide with an alkanethiol. The choice of the Lewis acid depends on the configuration of AcO-2, The carbohydrate-derived surfactants exhibit thermotropic liquid-crystalline behaviour. The alkyl 1-thioglycopyranosides form the expected smectic A phases upon heating. The clearing temperatures vary with alkyl chain length which is in accordance with the accepted model for the S-A phase of amphiphilic carbohydrate mesogens. For the alkyl 1-thiotalopyranosides, the clearing points are much lower than expected, presumably due to the formation of an intramolecular hydrogen bond in the talose moiety. (C) 1997 Elsevier Science Ltd.