propargyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside | 940933-63-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propargyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 940933-63-1
• 化学式: C₁₅H₂₀O₈
• 分子量: 328.319
• InChiKey: OOVKJRZVTPQGLW-TUVASFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  propargyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside 在 甲醇 、 sodium hydride 、 DOWEX-50H⁺ 作用下， 以 甲醇 为溶剂， 反应 1.03h， 以571 mg的产率得到propargyl 2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Traceless Chiral Auxiliaries for the Allene Ether Nazarov Cyclization

  摘要：

  The key stereochemical factors that determine transfer of asymmetry from the chiral auxiliary to the cyclopentenone in the allene ether version of the Nazarov reaction have been elucidated. On the basis of the new insights into the mechanism, two highly effective chiral auxiliaries were designed and prepared.

  DOI：

  10.1021/jo801503c
• 作为产物：
  描述：

  2-丙炔-1-醇 、 1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-arabinohexopyranose 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到
  参考文献：
  名称：

  α-Selective synthesis of 2-deoxy-glycosides and disaccharides

  摘要：

  A metal-free catalytic method for the synthesis of 2-deoxy glycosides and disaccharides has been developed using stable 2-deoxy glucosyl and galactosyl acetate donors. They could react with a variety of acceptors in the presence of catalytic amount of TMSOTf at 0 degrees C to form glycosides, glycoconjugates, and disaccharides with excellent alpha-selectivity (> 19:1) and yields (up to 99%) in a short time (0.5 h). With this expedient method, several new compounds against human K562 and SMMC7721 cell lines were obtained and tested with in vitro antitumor bioactivities.

  DOI：

  10.1080/07328303.2018.1439498