(2R,3R,4S,5S,6S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(3-phenylpropoxy)oxane | 160833-87-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R,4S,5S,6S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(3-phenylpropoxy)oxane
• CAS: 160833-87-4
• 化学式: C₄₃H₄₆O₆
• 分子量: 658.835
• InChiKey: GWVYXFXCNDPWRO-FYYRRIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 potassium tert-butylate 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 0.33h， 生成 (2R,3R,4S,5S,6S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(3-phenylpropoxy)oxane 、
  参考文献：
  名称：

  Mechanistic Study of Glycosylation Using a Prop-1-enyl Donor

  摘要：

  Studies have been conducted to elucidate the mechanism of glycosylation reactions using a prop-1-enyl donor isomerized directly from an allyl glycoside. The reactions promoted by NIS/TfOH can take place in high yields in acetonitrile at room temperature. Activation of the anomeric prop-1-enyl group often leads to both the desired glycoside (e.g., 9) and the addition-reaction product (e.g., the anomeric mixed acetal 10). TfOH perhaps has a dual role in the reaction: i.e., (a) producing IOTf in situ to activate the prop-1-enyl group and (b) catalyzing the transformation from the addition-reaction product to the desired glycoside (e.g., from 10 to 9). The latter process involves multiple competing pathways.

  DOI：

  10.1021/jo301664c

文献信息

• Mechanistic Study of Glycosylation Using a Prop-1-enyl Donor
  作者：Haishen Yang、Pengfei Wang

  DOI：10.1021/jo301664c

  日期：2013.3.1

  Studies have been conducted to elucidate the mechanism of glycosylation reactions using a prop-1-enyl donor isomerized directly from an allyl glycoside. The reactions promoted by NIS/TfOH can take place in high yields in acetonitrile at room temperature. Activation of the anomeric prop-1-enyl group often leads to both the desired glycoside (e.g., 9) and the addition-reaction product (e.g., the anomeric mixed acetal 10). TfOH perhaps has a dual role in the reaction: i.e., (a) producing IOTf in situ to activate the prop-1-enyl group and (b) catalyzing the transformation from the addition-reaction product to the desired glycoside (e.g., from 10 to 9). The latter process involves multiple competing pathways.