(1'R,2'S,3'R,4'S)-5-[2'-benzyloxy-3'-tert-butyldimethylsilyloxy-4',5'-dihydroxy-1'-(1H-indol-3-yl)-4',5'-di-O-isopropylidene-pentan-1'-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione | 1224111-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1'R,2'S,3'R,4'S)-5-[2'-benzyloxy-3'-tert-butyldimethylsilyloxy-4',5'-dihydroxy-1'-(1H-indol-3-yl)-4',5'-di-O-isopropylidene-pentan-1'-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 1224111-90-3
• 化学式: C₃₅H₄₇NO₈Si
• 分子量: 637.846
• InChiKey: UVNBJCGRLSRBBW-ZHTHUIBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  105.31
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  吲哚 、 丙二酸环(亚)异丙酯 、 溴甲苯 、 叔丁基二甲基氯硅烷 、 4,5-O-isopropylidene-L-arabinose di(ethylthio)acetal 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.5h， 以48%的产率得到(1'S,2'S,3'R,4'S)-5-[2'-benzyloxy-3'-tert-butyldimethylsilyloxy-4',5'-dihydroxy-1'-(1H-indol-3-yl)-4',5'-di-O-isopropylidene-pentan-1'-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Diastereoselective trimolecular condensation between indole, Meldrum’s acid and chiral sugar-derived aldehydes

  摘要：

  The trimolecular condensation of indole, Meldrum's acid and chiral, sugar-derived aldehydes took place in good yield and high diastereoselectivity. The absolute configuration of the alpha-carbon of the chiral aldehydes ensured a predictable diastereocontrol of the newly created stereogenic centre except for (3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[3,2-d][1,3]dioxole-5-carbaldehyde 3i. In this case, the opposite stereochemistry may be explained by a less congested conformer of the Knoevenagel-adduct intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.017