2-deoxy-1-thioglycoside | 144789-51-5

• 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: 2-deoxy-1-thioglycoside
• 英文别名: ethyl 2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-arabino-hexopyranoside；[(2R,3S,4R)-3,4-diacetyloxy-6-ethylsulfanyloxan-2-yl]methyl acetate
• CAS: 144789-51-5
• 化学式: C₁₄H₂₂O₇S
• 分子量: 334.39
• InChiKey: FTPWDDWCHUEJQV-VMXNZORSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-deoxy-1-thioglycoside 、 [(2R,3S,4R)-4-acetyloxy-3-hydroxy-6-phenylmethoxyoxan-2-yl]methyl acetate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis of 2-deoxy-d-arabino/lyxo-hexopyranosyl disaccharides

  摘要：

  Synthesis of 2-deoxy-D-arabino/lyxo-hexopyranosyl disaccharides is reported. In these, the disaccharides contain 2-deoxy-arabino-hexopyranosyl and 2-deoxy-lyxo-hexopyranosyl sugars as either the reducing or the non-reducing or both the sugar units of the disaccharides. The activated 2-deoxy-1-thioglycosides served as the common precursors to prepare the 2-deoxy disaccharides with the above configurations. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.11.017

文献信息

• Erosion of Stereochemical Control with Increasing Nucleophilicity: <i>O</i>-Glycosylation at the Diffusion Limit
  作者：Matthew G. Beaver、K. A. Woerpel

  DOI：10.1021/jo902222a

  日期：2010.2.19

  Nucleophilic substitution reactions of 2-deoxyglycosyl donors indicated that the reactivity of the oxygen nucleophile has a significant impact on stereoselectivity. Employing ethanol as the nucleophile resulted in a 1:1 (alpha:beta) ratio of diastereomers under S(N)1-like reaction conditions. Stercoselective formation of the 2-deoxy-alpha-O-glycoside was only observed when weaker nucleophiles, such as trifluoroethanol, were employed. The lack of stercoselectivity observed in reactions of common oxygen nucleophiles can be attributed to reaction rates of the stereochemistry-determining step that approach the diffusion limit. In this scenario, both faces of the prochiral oxocarbenium ion are subject to nucleophilic addition to afford a statistical mixture of diastercomeric products. Control experiments confirmed that all nucleophilic substitution reactions were performed under kinetic control.
• Effect of the C-2 hydroxyl group on the mesomorphism of alkyl glycosides: synthesis and thermotropic behavior of alkyl 2-deoxy-d-arabino-hexopyranosides
  作者：Madan Kumar Singh、Narayanaswamy Jayaraman、D.S. Shankar Rao、S. Krishna Prasad

  DOI：10.1016/j.chemphyslip.2008.07.008

  日期：2008.10

  A homologous series of alkyl 2-deoxy-alpha-D-arabino-hexopyranosides and alkyl 2-deoxy-beta-D-arabino-hexopyranosides were synthesized, upon glycosylation of 1-alkanols (from C-8 to C-18 alkanols) with ethyl 2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-arabino-hexopyranoside, followed by a deprotection. The thermotropic behavior of these new types of alkyl glycosides was investigated. It was observed that the beta-anomers of these alkyl glycosides, bearing nonyl to tetradecyl alkyl chain are mesomorphic, exhibiting monotropic smectic A phase. In contrast, the alpha-anomers are all non-mesomorphic. An effort to identify the liquid crystalline behavior of binary mixtures of the alpha- and beta-anomers was undertaken and it was found that mixtures containing equimolar amounts of the anomers exhibited rnesomorphic behavior. A fine balance of the hydrophilic and hydrophobic components within the molecule is also found to be important for the alkyl 2-deoxy glycosides to form the mesophase. (C) 2008 Elsevier Ireland Ltd. All rights reserved.
• Crystal structures and thermal analyses of alkyl 2-deoxy-α-d-arabino-hexopyranosides
  作者：Madan Kumar Singh、Diptikanta Swain、Tayur N. Guru Row、Narayanaswamy Jayaraman

  DOI：10.1016/j.carres.2009.06.024

  日期：2009.10

  The crystal structures of alkyl 2-deoxy-alpha-D-arabino-hexopyranosides, with the alkyl chain lengths from C(8) to C(18), are established by the single crystal X-ray structural determination. The even-alkyl chain length derivatives crystallized orthorhombic, with space group P2(1)2(1)2(1), whereas the odd-alkyl chain length derivatives crystallized monoclinic, with space group P2(1). The sugar moieties retained a (4)C(1) chair conformation and the conformation of the alkyl chains was all-trans. The molecules formed a bilayer structure, in which alkyl chains were interdigitated. The hydrogen bonds, originating from the sugar moieties, were observed in adjacent layers and also within the same layer, resulting in the formation of infinite chains. The alkyl chains arranged parallel to each other and formed planar structures. The thermal properties of the alkyl 2-deoxy glucosides were analyzed further. It was observed that none of the derivatives exhibited mesomorphism. This study establishes that the absence of the hydroxyl group at C-2 of the sugar moiety results in a non-mesogenic nature of the alkyl 2-deoxy-alpha-D-glycosides, as opposed to the profound mesogenic nature of the normal alkyl glycosides. (C) 2009 Elsevier Ltd. All rights reserved.