(3R,4S,5S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]oxolan-2-one | 874130-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4S,5S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]oxolan-2-one
• CAS: 874130-69-5
• 化学式: C₂₄H₅₂O₅Si₃
• 分子量: 504.93
• InChiKey: ZEXJESHEOTXRQI-FUMNGEBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]oxolan-2-one 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  Stereoselective C-glycosidation of d-fucose derivatives directed by the protective groups

  摘要：

  Stereoselectivity in the C-glycosidation of lactones derived from D-fucose by following Kishi's method, which involves the addition of a nucleophile onto a carbohydrate-derived lactone and subsequent reduction of the lactol, was found to be reliant on the nature of the C2 and C3 protective groups. Lactones bearing TBDMS protecting groups selectively afford 1,3-trans products (alpha anomer), in which the stereoselective outcome is in apparent concordance with Woerpel's model. On the other hand, their benzylated congeners produce the 1,3-cis products (beta anomer) as the major diastereoisomers. The latter results suggest an abnormal behavior during the stereoselective nucleophilic substitution at the anomeric position of the benzylated lactones. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.04.005

文献信息

• Stereoselective C-glycosidation of d-fucose derivatives directed by the protective groups
  作者：Omar Cortezano-Arellano、Camilo A. Meléndez-Becerra、Fernando Cortés、Fernando Sartillo-Piscil、Alejandro Cordero-Vargas

  DOI：10.1016/j.carres.2014.04.005

  日期：2014.7

  Stereoselectivity in the C-glycosidation of lactones derived from D-fucose by following Kishi's method, which involves the addition of a nucleophile onto a carbohydrate-derived lactone and subsequent reduction of the lactol, was found to be reliant on the nature of the C2 and C3 protective groups. Lactones bearing TBDMS protecting groups selectively afford 1,3-trans products (alpha anomer), in which the stereoselective outcome is in apparent concordance with Woerpel's model. On the other hand, their benzylated congeners produce the 1,3-cis products (beta anomer) as the major diastereoisomers. The latter results suggest an abnormal behavior during the stereoselective nucleophilic substitution at the anomeric position of the benzylated lactones. (C) 2014 Elsevier Ltd. All rights reserved.