(2R,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enyl-3-prop-2-ynoxyoxane | 1261295-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enyl-3-prop-2-ynoxyoxane
• CAS: 1261295-40-2
• 化学式: C₃₃H₃₆O₅
• 分子量: 512.646
• InChiKey: YZUZXNLROIAXPO-IZDBAANZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-(prop-2-ynyl)- α-D-glucopyranoside 、 烯丙基三甲基硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以90%的产率得到(2R,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enyl-3-prop-2-ynoxyoxane
  参考文献：
  名称：

  Ultrasound-assisted synthesis of C-glycosides

  摘要：

  A significant rate enhancement was observed in the preparation of allyl and allenyl-C-glycosides from glycosyl acetate or methyl O-glycoside precursors when ultrasound irradiation was employed as an energy source. The C-glycosides were obtained in 77-96% yields in <20 min using TMSOTf as promoter. These results show that sonication provides rapid and efficient access to useful C-glycoside-based building blocks. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.113

文献信息

• Ultrasound-assisted synthesis of C-glycosides
  作者：Dilip V. Jarikote、Ciaran O’Reilly、Paul V. Murphy

  DOI：10.1016/j.tetlet.2010.10.113

  日期：2010.12

  A significant rate enhancement was observed in the preparation of allyl and allenyl-C-glycosides from glycosyl acetate or methyl O-glycoside precursors when ultrasound irradiation was employed as an energy source. The C-glycosides were obtained in 77-96% yields in <20 min using TMSOTf as promoter. These results show that sonication provides rapid and efficient access to useful C-glycoside-based building blocks. (C) 2010 Elsevier Ltd. All rights reserved.