methyl 4,6-O-benzylidene-3-O-p-toluenesulfonyl-β-D-galactopyranoside | 86470-08-8

• 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: methyl 4,6-O-benzylidene-3-O-p-toluenesulfonyl-β-D-galactopyranoside
• 英文别名: methyl 4,6-O-benzylidene-3-O-p-toluenesulfonyl-β-D-galactoside；methyl 4,6-O-benzylidene-β-D-galactopyranoside 3-O-p-toluenesulfonate；methyl-[O⁴,O⁶-((S)-benzylidene)-O³-(toluene-4-sulfonyl)-β-D-galactopyranoside]；Methyl-[O⁴,O⁶-((S)-benzyliden)-O³-(toluol-4-sulfonyl)-β-D-galactopyranosid]；[(2S,4aR,6R,7R,8R,8aS)-7-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 4-methylbenzenesulfonate
• CAS: 86470-08-8
• 化学式: C₂₁H₂₄O₈S
• 分子量: 436.483
• InChiKey: ILVUHCKVCFKMOA-OXZADQLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-3-O-p-toluenesulfonyl-β-D-galactopyranoside 在 甲醇 、 sodium amalgam 、 silver(l) oxide 、 碘甲烷 作用下， 生成 methyl 4,6-O-benzylidene-2-O-methyl-β-D-galactopyranoside
  参考文献：
  名称：

  d-理想a d（+）-半乳糖

  摘要：

  DOI：

  10.1002/hlca.19450280102
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 吡啶 、 氯仿 、 苯甲醛 、 zinc(II) chloride 作用下， 生成 methyl 4,6-O-benzylidene-3-O-p-toluenesulfonyl-β-D-galactopyranoside
  参考文献：
  名称：

  d-理想a d（+）-半乳糖

  摘要：

  DOI：

  10.1002/hlca.19450280102

文献信息

• Highly Efficient Selective Benzylation of Carbohydrates Catalyzed by Iron(III) with Silver Oxide and Bromide Anion as Co-catalysts
  作者：Bo Ren、Jian Lv、Yu Zhang、Jun Tian、Hai Dong

  DOI：10.1002/cctc.201601558

  日期：2017.3.20

  and polyols was developed. With the use of Ag2O (0.6 equiv.) and tetrabutylammonium bromide (0.1 equiv.) as co‐catalysts, the iron(III)‐catalyzed benzylation reaction proceeded to completion at 40 °C within 2–3 h and gave the products in high yields with high regioselectivities. A mechanism involving the principle of enhanced basicity of Ag2O by soft anions was proposed.

  开发了一种高效，绿色和区域选择性的二醇和多元醇苄基化方法。通过使用Ag 2 O（0.6当量）和四丁基溴化铵（0.1当量）作为助催化剂，铁（III）催化的苄基化反应在40°C的2-3小时内完成，得到了产物。高收率和高区域选择性。提出了一种通过软阴离子增强Ag 2 O碱度的原理的机理。
• Base-Promoted Rearrangement of Sugar Epoxides to Unsaturated Sugars
  作者：Yuan Wang、Qin Li、Shuihong Cheng、Yanfen Wu、Dongjie Guo、Qiu-Hua Fan、Xiaofang Wang、Li-He Zhang、Xin-Shan Ye

  DOI：10.1021/ol052128x

  日期：2005.12.1

  [chemical reaction: see text]. A simple and efficient method for rearranging 2,3-anhydro carbohydrates to unsaturated sugars has been developed. The exceptionally mild reaction conditions and high stereoselectivity should make this an attractive method for the preparation of unsaturated carbohydrate derivatives.

  [化学反应：见正文]。已经开发了一种简单有效的方法，用于将2，3-脱水碳水化合物重新排列为不饱和糖。异常温和的反应条件和高立体选择性应使其成为制备不饱和碳水化合物衍生物的有吸引力的方法。
• Synthesis of 3-amido-3-deoxy-β-d-talopyranosides: all-cis-substituted pyranosides as lectin inhibitors
  作者：Christopher T. Öberg、Ann-Louise Noresson、Hakon Leffler、Ulf J. Nilsson

  DOI：10.1016/j.tet.2011.09.098

  日期：2011.11

  3-Deoxy-3-amino-beta-D-talopyranosides have been synthesized for the first time. The amines were obtained from galactopyranosides through 2,3-anhydrogulosides that were opened to idosides followed by an oxidation/reductive amination sequence. From the amines, 11 corresponding 3-deoxy-3-arylamido-beta-talopyranosides have been synthesized and evaluated as inhibitors against galectin-1, -2, -3, -4C, -4N, -7, -8N and -9N. The synthesized talosamides showed selectivity for Galectin-4C with three of the mono-saccharides having dissociation constants at around 100 mu M against the lectin, which is more than two orders of magnitude better than methyl beta-galactoside and significantly better than the previous best galectin-4C monosaccharide inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.
• Szeja, Wieslaw, Polish Journal of Chemistry, 1981, vol. 55, # 9, p. 1803 - 1808
  作者：Szeja, Wieslaw

  DOI：——

  日期：——
• Engelhardt, Lutz M.; Mocerino, Mauro; Stick, Robert V., Australian Journal of Chemistry, 1990, vol. 43, # 6, p. 1111 - 1117
  作者：Engelhardt, Lutz M.、Mocerino, Mauro、Stick, Robert V.、White, Allan H.

  DOI：——

  日期：——