2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-galactosyl bromide | 13046-90-7

• 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: 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-galactosyl bromide
• 英文别名: 2,3,4-tri-O-acetyl-6-O-tosyl-α-D-galactopyranosyl bromide；2,3,4-Tri-O-acetyl-6-tosyl-α-D-galactopyranosyl bromide；O²,O³,O⁴-triacetyl-O⁶-(toluene-4-sulfonyl)-α-D-galactopyranosyl bromide；O²,O³,O⁴-Triacetyl-O⁶-(toluol-4-sulfonyl)-α-D-galactopyranosylbromid；2,3,4-Tri-O-acetyl-6-O-p-tolylsulfonyl-α-D-galactopyranosylbromid；(2R,3R,4S,5S,6R)-2-Bromo-6-((tosyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate；[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-bromo-2-[(4-methylphenyl)sulfonyloxymethyl]oxan-3-yl] acetate
• CAS: 13046-90-7
• 化学式: C₁₉H₂₃BrO₁₀S
• 分子量: 523.356
• InChiKey: QEJSZXDTRCRCHO-SPOLIRPYSA-N

物化性质

• 熔点：
  147 °C
• 沸点：
  556.5±50.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-galactosyl bromide 在 盐酸 、 甲醇 、 sodium hydroxide 、 sodium 、 丙酮 、 silver carbonate 、 silver(l) oxide 作用下， 生成 O2,O4-Dimethyl-3,6-anhydro-D-galactose-dimethylacetal
  参考文献：
  名称：

  Haworth et al., Journal of the Chemical Society, 1940, p. 620,629

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-(p-tolylsulfonyl)-β-D-galactopyranose 在 氢溴酸 、 溶剂黄146 作用下， 生成 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-galactosyl bromide
  参考文献：
  名称：

  Ohle; Thiel, Chemische Berichte, 1933, vol. 66, p. 525,531

  摘要：

  DOI：

文献信息

• A New Approach to Some 1,6-Dideoxy 1,6-Epithio Sugars
  作者：H Driguez、JC Mcauliffe、RV Stick、DMG Tilbrook、SJ Williams

  DOI：10.1071/ch9960343

  日期：——

  The treatment of hexopyranosyl bromides, also activated at C6 (Br, OTs, OMs), with H2S/HCONMe2 under basic conditions gives rise to 1,6-dideoxy 1,6-epithio sugars. One such sugar has been further transformed into the synthetically useful 3,4-anhydro-1,6-dideoxy-1,6-epithio-β-D-galactose. The treatment of this epoxide with sodium azide and with cyclohexylamine is described. An analogous treatment of one doubly activated hexopyranosyl bromide with sodium hydrogen selenide has led to a novel 1,6-dideoxy 1,6-episeleno sugar which displayed interesting n.m.r. spectra. Finally, in an attempt to prepare 1,6-dideoxy 1,6-epidithio sugars, a tetraalkylammonium tetrathiomolybdate reagent was found to be the reagent of choice for converting doubly activated hexopyranosyl bromides into 1,6-dideoxy 1,6-epithio sugars.

  在碱性条件下，用 H2S/HCONMe2 处理同样在 C6 处活化的溴化六吡喃糖（Br、OTs、OMs），会产生 1,6-二脱氧 1,6-epithio 糖。其中一种糖被进一步转化为对合成有用的 3,4-脱氢-1,6-二脱氧-1,6-环硫代-β-D-半乳糖。文中介绍了用叠氮化钠和环己胺处理这种环氧化物的方法。用硒化氢钠对一种双活化的溴化六吡喃糖进行类似处理后，得到了一种新型的 1,6-二脱氧 1,6-episeleno 糖，它显示出有趣的 n.m.r. 光谱。最后，在尝试制备 1,6-二脱氧 1,6-epidithio 糖时，发现四烷基钼酸四铵试剂是将双活化溴化己吡喃糖基转化为 1,6-二脱氧 1,6-epithio 糖的首选试剂。
• Synthesis of a cyanoethylidene derivative of 3,6-anhydro-d-galactose and its application as glycosyl donor
  作者：Christian Vogel、Galina Morales Torres、Helmut Reinke、Dirk Michalik、Alice Voss

  DOI：10.1016/j.carres.2006.09.015

  日期：2007.2

  corresponding bromide and both cyanoethylidene derivatives were used as donors in glycosylation reactions. The coupling with benzyl 2,4,6-tri-O-acetyl-3-O-trityl-beta-d-galactopyranoside provided exclusively the beta-linked disaccharides in approximately 30% yield. The more reactive methyl 2,3-O-isopropylidene-4-O-trityl-alpha-l-rhamnopyranoside gave with donors 3 and 7 the corresponding disaccharides in

  从1,2,4-三-O-乙酰基-3,6-脱水-α-d-吡喃半乳糖开始，4-O-乙酰基-3,6-脱水-1,2-O-（1-氰基亚乙基）-通过用氰基三甲基硅烷处理合成了α-d-吡喃半乳糖（7）。另外，由相应的溴化物制备了3,4-二-O-乙酰基-1,2-O-（1-氰基亚乙基）-6-O-甲苯磺酰基-α-d-吡喃半乳糖，并且将两种氰基亚乙基衍生物用作供体。糖基化反应。与苄基2,4,6-三-O-乙酰基-3-O-三苯甲基-β-d-吡喃半乳糖苷的偶联仅以约30％的收率提供了β-连接的二糖。反应性更高的甲基2,3-O-异亚丙基-4-O-三苯甲基-α-1-鼠李糖吡喃糖苷与供体3和7一起以接近60％的收率得到相应的二糖。此外，合成了3,6-脱水-4-O-三苯甲基-1,2-O- [1-（氰基氰基）亚乙基]-α-d-吡喃半乳糖，
• A simple and convenient method for the synthesis of pyranoid glycals
  作者：Jinzhong Zhao、Shanqiao Wei、Xiaofeng Ma、Huawu Shao

  DOI：10.1016/j.carres.2009.10.003

  日期：2010.1

  A simple, mild, and environmentally benign synthesis procedure of pyranoid glycals is described. In a novel fashion, protected glycopyranosyl bromides undergo the reductive elimination in the presence of zinc in phosphate buffer at room temperature. The pyranoid glycals were obtained in good-to-excellent yields (18 examples).

  描述了一种简单，温和的，对环境有益的吡喃糖类合成方法。以新颖的方式，在室温下在磷酸盐缓冲液中存在锌的情况下，受保护的吡喃葡萄糖基溴化物经历了还原消除。以良好至优异的产率获得了吡喃类糖（18个实施例）。
• A mild and environmentally benign method for the synthesis of glycals in PEG-600/H2O
  作者：Jinzhong Zhao、Shanqiao Wei、Xiaofeng Ma、Huawu Shao

  DOI：10.1039/b821681a

  日期：——

  Glycals were synthesized via a simple, mild, convenient and environmentally benign procedure, in which protected glycosyl bromides undergo the reductive elimination in the presence of zinc in PEG-600/H2O at room temperature. The glycals were obtained in 75–92% isolated yields.

  糖醇通过一种简单、温和、方便且环保的程序合成，在该过程中，保护的糖苷溴化物在室温下与锌在PEG-600/H2O的存在下进行还原消除反应。糖醇的分离产率为75-92%。
• A Rapid Synthesis of Pyranoid Glycals Promoted by β-Cyclodextrin and Ultrasound
  作者：Jinzhong Zhao、Huawu Shao、Xin Wu、Shaojing Shi

  DOI：10.1002/cjoc.201180263

  日期：2011.7

  procedure for the synthesis of glycals from glycosyl bromides with very low zinc dust loading (1.5 equiv.) is described. The process is activated by β‐cyclodextrin and ultrasound. Based on 19 samples, this method has been demonstrated to be highly effective for a broad range of glycosyl bromides, including acid‐ or base‐sensitive and disaccharide glycosyl bromides. A yield of 85%–96% of glycals was obtained

  描述了一种从糖基溴化物中合成锌粉的负荷非常低（1.5当量）的便捷且环境友好的方法。β-环糊精和超声波可激活该过程。基于19个样品，该方法已被证明对多种糖基溴化物都非常有效，包括对酸或碱敏感的二糖基糖基溴化物。获得了85％–96％的缩醛收率。