(2R,4R)-1,2-O-isopropylidene-4-methylpentan-3-one-1,2,5-triol | 591749-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R)-1,2-O-isopropylidene-4-methylpentan-3-one-1,2,5-triol
• 英文别名: (2R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2-methylpropan-1-one
• CAS: 591749-74-5
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: WYAYPRRIIWYWHP-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1,2-O-isopropylidene-4-methylpentan-3-one-1,2,5-triol 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 (2R,3R,4R)-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetraol 、 (1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropane-1,3-diol
  参考文献：
  名称：

  Application of a New Tandem Isomerization−Aldolization Reaction of Allylic Alcohols to the Synthesis of Three Diastereoisomers of (2R)-1,2-O-Isopropylidene-4-methylpentane-1,2,3,5-tetraol

  摘要：

  The tandem isomerization-aldolization reaction of (2R)-1,2-O-isopropylidene-4-penten-1,2,3-triol 3 and formaldehyde gives a mixture of two aldol products 2a and 2b. The stereoselective reduction of each compound by L-Selectride affords two diastereoisomers of (2R)-1,2-O-Isopropylidene-4-methylpentane-1,2,3,5-tetraol while a third diastereoisomer is obtained by stereoselective reduction with Me4NHB(OAc)(3).

  DOI：

  10.1021/jo0342727
• 作为产物：
  描述：

  (4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol 在 吡啶 、 咪唑 、 五羰基铁 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 99.5h， 生成 (2R,4R)-1,2-O-isopropylidene-4-methylpentan-3-one-1,2,5-triol
  参考文献：
  名称：

  Application of a New Tandem Isomerization−Aldolization Reaction of Allylic Alcohols to the Synthesis of Three Diastereoisomers of (2R)-1,2-O-Isopropylidene-4-methylpentane-1,2,3,5-tetraol

  摘要：

  The tandem isomerization-aldolization reaction of (2R)-1,2-O-isopropylidene-4-penten-1,2,3-triol 3 and formaldehyde gives a mixture of two aldol products 2a and 2b. The stereoselective reduction of each compound by L-Selectride affords two diastereoisomers of (2R)-1,2-O-Isopropylidene-4-methylpentane-1,2,3,5-tetraol while a third diastereoisomer is obtained by stereoselective reduction with Me4NHB(OAc)(3).

  DOI：

  10.1021/jo0342727

文献信息

• Application of a New Tandem Isomerization−Aldolization Reaction of Allylic Alcohols to the Synthesis of Three Diastereoisomers of (2<i>R</i>)-1,2-<i>O</i>-Isopropylidene-4-methylpentane-1,2,3,5-tetraol
  作者：David Cuperly、Christophe Crévisy、René Grée

  DOI：10.1021/jo0342727

  日期：2003.8.1

  The tandem isomerization-aldolization reaction of (2R)-1,2-O-isopropylidene-4-penten-1,2,3-triol 3 and formaldehyde gives a mixture of two aldol products 2a and 2b. The stereoselective reduction of each compound by L-Selectride affords two diastereoisomers of (2R)-1,2-O-Isopropylidene-4-methylpentane-1,2,3,5-tetraol while a third diastereoisomer is obtained by stereoselective reduction with Me4NHB(OAc)(3).