(2R,4R)-1,2-O-isopropylidene-5-O-tert-butyldimethylsilyl-4-methylpentan-3-one-1,2,5-triol | 124317-88-0

• 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-5-O-tert-butyldimethylsilyl-4-methylpentan-3-one-1,2,5-triol
• 英文别名: (2R)-3-[tert-butyl(dimethyl)silyl]oxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylpropan-1-one
• CAS: 124317-88-0
• 化学式: C₁₅H₃₀O₄Si
• 分子量: 302.486
• InChiKey: LPNBVOPSVNLYAC-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1,2-O-isopropylidene-5-O-tert-butyldimethylsilyl-4-methylpentan-3-one-1,2,5-triol 在 吡啶 、 氟化氢吡啶 、 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 97.0h， 生成 (2R,3R,4R)-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetraol
  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 咪唑 、 五羰基铁 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (2R,4R)-1,2-O-isopropylidene-5-O-tert-butyldimethylsilyl-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

• Scheuplein, Stefan W.; Kusche, Andreas; Brueckner, Reinhard, Chemische Berichte, 1990, vol. 123, # 4, p. 917 - 925
  作者：Scheuplein, Stefan W.、Kusche, Andreas、Brueckner, Reinhard、Harms, Klaus

  DOI：——

  日期：——
• 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).