2,3,4,6-tetra-O-acetyl-β-D-sulfonylpropynylgalactopyranoside | 1159101-97-9

• 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: 2,3,4,6-tetra-O-acetyl-β-D-sulfonylpropynylgalactopyranoside
• CAS: 1159101-97-9
• 化学式: C₁₇H₂₂O₁₁S
• 分子量: 434.421
• InChiKey: CBKSVKSTHDBIAX-HMDCTGQHSA-N

物化性质

• 沸点：
  546.7±50.0 °C(predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.88
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  148.57
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-sulfonylpropynylgalactopyranoside 、 4-azidobenzenesulfonamide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以66%的产率得到4-(4-{[2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl]sulfonylmethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Inhibition of carbonic anhydrase isozymes with benzene sulfonamides incorporating thio, sulfinyl and sulfonyl glycoside moieties

  摘要：

  A series of benzene sulfonamides incorporating thio, sulfinyl or sulfonyl glycoside moieties were synthesized. These glycoconjugates were investigated for their ability to inhibit the enzymatic activity of four human carbonic anhydrases (hCA): isozymes I, II and tumour-associated isozymes IX and XII. The oxidation state of the sulfur in the carbohydrate tail moiety did not influence either enzyme inhibition potency or isozyme selectivity even though presenting opportunities for differing interactions with the target isozymes. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.086
• 作为产物：
  描述：

  propargyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到2,3,4,6-tetra-O-acetyl-β-D-sulfonylpropynylgalactopyranoside
  参考文献：
  名称：

  Inhibition of carbonic anhydrase isozymes with benzene sulfonamides incorporating thio, sulfinyl and sulfonyl glycoside moieties

  摘要：

  A series of benzene sulfonamides incorporating thio, sulfinyl or sulfonyl glycoside moieties were synthesized. These glycoconjugates were investigated for their ability to inhibit the enzymatic activity of four human carbonic anhydrases (hCA): isozymes I, II and tumour-associated isozymes IX and XII. The oxidation state of the sulfur in the carbohydrate tail moiety did not influence either enzyme inhibition potency or isozyme selectivity even though presenting opportunities for differing interactions with the target isozymes. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.086

文献信息

• Copper-catalyzed one-pot synthesis of glycosylated iminocoumarins and 3-triazolyl-2-iminocoumarins
  作者：Pintu Kumar Mandal

  DOI：10.1039/c3ra46844e

  日期：——

  general strategy was developed for the synthesis of glycosyl iminocoumarins (5a–x) in a one-pot, copper-catalyzed multicomponent reaction involving a domino reaction of sulfonyl azides, sugar alkynes, and salicylaldehydes via ketenimine intermediate formation. Similarly, glycosyl 3-triazolyl-2-iminocoumarin derivatives (6a–o) have also been synthesized in a one-pot, three component condensation via tandem

  已开发了在单罐，铜催化的多组分反应中合成糖基亚氨基香豆素（5a–x）的通用策略，该反应涉及通过乙炔亚胺中间体形成的磺酰叠氮化物，糖炔和水杨醛的多米诺反应。同样，糖基3-三唑基-2-亚氨基香豆素衍生物（6a-o）也已通过串联的“ CuAAC-醛醇-环化-脱水”序列以一锅，三组分缩合的方式合成。在这种情况下，2-叠氮基乙腈和糖炔之间的铜催化环加成反应可原位提供三唑衍生物。并活化了相邻的亚甲基，在水杨醛存在下诱导了羟醛-环化-脱水序列。在所有反应中收率都非常好。