1,5-dideoxy-5-thio-L-iditol | 1404084-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 1,5-dideoxy-5-thio-L-iditol
• 英文别名: 1-deoxythioidonojirimycin；SId；(2S,3S,4R,5R)-2-(hydroxymethyl)thiane-3,4,5-triol
• CAS: 1404084-94-1
• 化学式: C₆H₁₂O₄S
• 分子量: 180.225
• InChiKey: IHFROQCVGFICCX-UNTFVMJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-古洛糖酸-gamma-内酯 在 potassium fluoride 、 benzyltriethylammonium tetrathiomolybdate 、 氢溴酸 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 丙酮 、 乙腈 为溶剂， 反应 35.5h， 生成 1,5-dideoxy-5-thio-L-iditol
  参考文献：
  名称：

  具有来自 L-Gulono-1,4-内酯和 D-Glycero-D-gulo-heptano-1,4-内酯的呋喃、吡喃诺和 Septano 基序的脱氧硫糖衍生物

  摘要：

  从 L-gulono-1,4-内酯和 D-glucoheptono-1,4-内酯开始，已经实现了模拟呋喃糖、吡喃糖和七糖结构的硫糖衍生物的短合成。合成中使用的不同策略是：（1）亲核置换和迈克尔加成；(2)环氧化物开环和迈克尔加成；(3)环氧化物开环亲核​​置换过程；(4) 双亲核置换。所有这些反应都使用四硫代钼酸苄基三乙基铵，(BnEt3N)(2)MoS4 作为硫转移试剂。

  DOI：

  10.1002/ejoc.201200906

文献信息

• De novo synthesis of 1-deoxythiosugars
  作者：Thanikachalam Gunasundari、Srinivasan Chandrasekaran

  DOI：10.1016/j.carres.2013.09.009

  日期：2013.12

  biologically potent and novel 1-deoxythiosugars is accomplished. Introduction of sulfur mediated by benzyltriethylammonium tetrathiomolybdate, as a sulfur transfer reagent through nucleophilic double displacement of tosylate in alpha,omega-di-O-tosyl aldonolactones in an intramolecular fashion is the key feature. The subsequent reduction of thiosugar lactones with borohydride exchange resin (BER) offers a

  完成了有效且新颖的具有生物活性的新型1-脱氧硫糖的化学合成。通过硫代甲酸酯以α，ω-二-O-甲苯磺酰基内酯内酯的亲核双取代以分子内方式引入作为硫转移剂的苄基三乙基铵四硫代钼酸铵是主要特征。随后用硼氢化物交换树脂（BER）还原硫糖内酯可提供许多脱氧硫糖，总收率良好。
• Preventing Protein Oxidation with Sugars: Scavenging of Hypohalous Acids by 5-Selenopyranose and 4-Selenofuranose Derivatives
  作者：Corin Storkey、David I. Pattison、Jonathan M. White、Carl H. Schiesser、Michael J. Davies

  DOI：10.1021/tx3003593

  日期：2012.11.19

  Heme peroxidases including myeloperoxidase (MPO) are released at sites of inflammation by activated leukocytes. MPO generates hypohalous acids (HOX, X = Cl, Br, SCN) from H2O2; these oxidants are bactericidal and are key components of the inflammatory response. However, excessive, misplaced or mistimed production can result in host tissue damage, with this implicated in multiple inflammatory diseases. We report here methods for the conversion of simple monosaccharide sugars into selenium- and sulfur-containing species that may act as potent water-soluble scavengers of HOX. Competition kinetic studies show that the seleno species react with HOC with rate constants in the range 0.8-1.0 X 10(8) M-1 s(-1), only marginally slower than those for the most susceptible biological targets including the endogenous antioxidant, glutathione. The rate constants for the corresponding sulfur sugars are considerably slower (1.4-1.9 X 10(6) M-1 s(-1)). Rate constants for reaction of the seleno-sugars with HOBr are, similar to 8 times lower than those for HOCl (1.0-1.5 X 10(7) M-1 s(-1)). These values show little variation with differing sugar structures. Reaction with HOSCN is slower (similar to 10(2) M-1 s(-1)) The seleno-sugars decreased the extent of HOCI-mediated oxidation of Met, His, Tip, Lys, and Tyr residues, and 3-chlorotyrosine formation, on both isolated bovine serum albumin and human plasma proteins, at concentrations as low as 50 mu M. These studies demonstrate that novel selenium (and to a lesser extent, sulfur) derivatives of monosaccharides could be potent modulators of peroxidase-mediated damage at sites of acute and chronic inflammation, and in multiple human pathologies.
• Deoxythiosugar Derivatives with Furano, Pyrano, and Septano Motifs from<scp>L</scp>-Gulono-1,4-lactone and<scp>D</scp>-Glycero-<scp>D</scp>-<i>gulo</i>-heptono-1,4-lactone
  作者：Thanikachalam Gunasundari、Srinivasan Chandrasekaran

  DOI：10.1002/ejoc.201200906

  日期：2012.12

  opening and Michael addition; (3) epoxide ring opening and nucleophilic displacement process; and (4) double nucleophilic displacement. All of these reactions used benzyltriethylammonium tetrathiomolybdate, (BnEt3N)(2)MoS4 as the sulfur-transfer reagent.

  从 L-gulono-1,4-内酯和 D-glucoheptono-1,4-内酯开始，已经实现了模拟呋喃糖、吡喃糖和七糖结构的硫糖衍生物的短合成。合成中使用的不同策略是：（1）亲核置换和迈克尔加成；(2)环氧化物开环和迈克尔加成；(3)环氧化物开环亲核​​置换过程；(4) 双亲核置换。所有这些反应都使用四硫代钼酸苄基三乙基铵，(BnEt3N)(2)MoS4 作为硫转移试剂。