ethyl 2,3-di-O-benzoyl-4,6-dideoxy-1-thio-α-L-lyxo-hexopyranoside | 260969-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2,3-di-O-benzoyl-4,6-dideoxy-1-thio-α-L-lyxo-hexopyranoside
• 英文别名: [(2S,3R,4R,6S)-3-benzoyloxy-2-ethylsulfanyl-6-methyloxan-4-yl] benzoate
• CAS: 260969-99-1
• 化学式: C₂₂H₂₄O₅S
• 分子量: 400.496
• InChiKey: NGIWBMSIJGZRRV-KBZIOIMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-di-O-benzoyl-4,6-dideoxy-1-thio-α-L-lyxo-hexopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 benzyl 4',6'-dideoxy-α-L-lyxo-hexopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Analogues of the mycobacterial arabinogalactan linkage disaccharide as cell wall biosynthesis inhibitors

  摘要：

  The mycobacterial arabinogalactan linkage disaccharide [alpha-(L)-Rha-(1 --> 3)-alpha-D-GlcNAc] provides a basis for the design of new antitubercular drugs, since it supports a key skeletal structure in the bacterial cell wall. A series of analogues of the linker was synthesized by coupling appropriate thiorhamnosyl donors modified at their 4-positions, with an N-acetyl glucosamine acceptor. In a cell-free enzyme inhibition assay, three analogues inhibited the activity of the galactosyltransferase that adds a Galf residue to the linkage disaccharide. Although the compounds were modest inhibitors, these data confirm the viability of this approach to anti-mycobacterial agents. It is especially significant that the three effective compounds are modified at the site of the acceptor atom in the natural substrate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00366-3
• 作为产物：
  描述：

  ethyl 1-thio-α-L-rhamnopyranoside 在 吡啶 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.33h， 生成 ethyl 2,3-di-O-benzoyl-4,6-dideoxy-1-thio-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  甲基（4,6-二脱氧-α-1-lyxo-己吡喃糖基）-（1→3）-和（4-脱氧-4-氟-α-1-鼠李糖基吡喃糖基）-（1→3）-2-的合成乙酰胺基-2-脱氧-α-d-吡喃葡萄糖苷，分枝杆菌阿拉伯半乳聚糖键联二糖的类似物

  摘要：

  摘要我们为4，6-二脱氧-1-Lyxo-己吡喃糖基（'4-deoxy-1-rhamnosyl'）和4-deoxy-4-fluoro-1-rhamnosyl单糖残基制备了硫代糖苷供体。脱氧氟鼠李糖的制备并不简单，并且揭示了二乙基氨基三氟化硫（DAST）试剂的某些出乎意料的行为。新的糖基供体用于合成分枝杆菌阿拉伯半乳聚糖键合二糖→4）-α-1-Rha-（1→3）-α-d-GlcNAc的两个类似物。这些类似物是分枝杆菌细胞壁构建早期阶段所涉及的酶的潜在抑制剂家族的原型。

  DOI：

  10.1016/s0008-6215(99)00203-7

文献信息

• Syntheses of methyl (4,6-dideoxy-α-l-lyxo-hexopyranosyl)-(1→3)- and (4-deoxy-4-fluoro-α-l-rhamnopyranosyl)-(1→3)-2-acetamido-2-deoxy-α-d-glucopyranosides, analogs of the mycobacterial arabinogalactan linkage disaccharide
  作者：Philip G. Hultin、Ryan M. Buffie

  DOI：10.1016/s0008-6215(99)00203-7

  日期：1999.11

  6-dideoxy- l - lyxo -hexopyranosyl (‘4-deoxy- l -rhamnosyl’) and 4-deoxy-4-fluoro- l -rhamnosyl monosaccharide residues. The preparation of the deoxyfluororhamnose was not straightforward, and revealed some unexpected behavior of the diethylaminosulfur trifluoride (DAST) reagent. The new glycosyl donors were used to synthesize two analogs of the mycobacterial arabinogalactan linkage disaccharide →4)-α- l

  摘要我们为4，6-二脱氧-1-Lyxo-己吡喃糖基（'4-deoxy-1-rhamnosyl'）和4-deoxy-4-fluoro-1-rhamnosyl单糖残基制备了硫代糖苷供体。脱氧氟鼠李糖的制备并不简单，并且揭示了二乙基氨基三氟化硫（DAST）试剂的某些出乎意料的行为。新的糖基供体用于合成分枝杆菌阿拉伯半乳聚糖键合二糖→4）-α-1-Rha-（1→3）-α-d-GlcNAc的两个类似物。这些类似物是分枝杆菌细胞壁构建早期阶段所涉及的酶的潜在抑制剂家族的原型。
• Analogues of the mycobacterial arabinogalactan linkage disaccharide as cell wall biosynthesis inhibitors
  作者：Xianghui Wen、Dean C Crick、Patrick J Brennan、Philip G Hultin

  DOI：10.1016/s0968-0896(03)00366-3

  日期：2003.8

  The mycobacterial arabinogalactan linkage disaccharide [alpha-(L)-Rha-(1 --> 3)-alpha-D-GlcNAc] provides a basis for the design of new antitubercular drugs, since it supports a key skeletal structure in the bacterial cell wall. A series of analogues of the linker was synthesized by coupling appropriate thiorhamnosyl donors modified at their 4-positions, with an N-acetyl glucosamine acceptor. In a cell-free enzyme inhibition assay, three analogues inhibited the activity of the galactosyltransferase that adds a Galf residue to the linkage disaccharide. Although the compounds were modest inhibitors, these data confirm the viability of this approach to anti-mycobacterial agents. It is especially significant that the three effective compounds are modified at the site of the acceptor atom in the natural substrate. (C) 2003 Elsevier Ltd. All rights reserved.