1,2;5,6-Di-O-isopropyliden-D-talitol | 53735-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2;5,6-Di-O-isopropyliden-D-talitol
• 英文别名: (1R,2S)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 53735-99-2
• 化学式: C₁₂H₂₂O₆
• 分子量: 262.303
• InChiKey: ODYBCPSCYHAGHA-KYXWUPHJSA-N

物化性质

• 熔点：
  64.5-65.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  382.0±32.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2;5,6-Di-O-isopropyliden-D-talitol 在 sodium periodate 、 碳酸氢钠 、 sodium sulfate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛
  参考文献：
  名称：

  Ruthenium-Catalyzed Asymmetric N-Demethylative Rearrangement of Isoxazolidines and Its Application in the Asymmetric Total Syntheses of (−)-(1R,3S)-HPA-12 and (+)-(1S,3R)-HPA-12

  摘要：

  An asymmetric N-demethylative rearrangement of 1,2-isoxazolidines catalyzed by ruthenium is described. Enantioenriched syn-1,3-aminoalcohols as well as cis-1,3-oxazinanes, which are useful building blocks, can be efficiently prepared stereospecifically by this reaction in good yields, via the isoxazolidine intermediates in situ generated from a nitrone bearing a chiral auxiliary and styrenes. This asymmetric reaction was also applied in the asymmetric total syntheses of both (-)-(1R,3S)-HPA-12 and (+)-(1S,3R)-HPA-12.

  DOI：

  10.1021/ol503261h
• 作为产物：
  描述：

  O³-benzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-mannitol 在 吡啶 、 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 1,2;5,6-Di-O-isopropyliden-D-talitol
  参考文献：
  名称：

  Crystalline 4-O-Benzoyl-1,2:5,6-di-O-isopropylidene-D-arabo-3-hexulose. A New Route to Talitol Derivatives

  摘要：

  DOI：

  10.1021/ja01578a051

文献信息

• Rhodium catalysed asymmetric hydroformylation with chiral diphosphite ligands
  作者：Godfried J.H. Buisman、Paul C.J. Kamer、Piet W.N.M. van Leeuwen

  DOI：10.1016/s0957-4166(00)80370-5

  日期：1993.7

  symmetry and have been used as ligands in the rhodium catalysed asymmetric hydroformylation of styrene. The catalytic activity of the diphosphites strongly depends on the bulkyness of the ligand. With a bulky ligand enantiomeric excesses up till 20% have been obtained under mild reaction conditions (25–40°C, 40 bar syngas). It was found that both enantiomeric excess and regioselectivity to the branched

  从1,2：5,6-二异亚丙基-D-甘露醇，L- α，α，α，α，-四甲基-1,3-二氧戊环-4,5-二甲醇和L-酒石酸二乙酯开始合成手性二亚磷酸酯。二醇在中度至良好的产率与反应2,2'- bisphenoxyphosphorus氯化物和4,4'，6,6'， -四-吨-丁基-2,2'- bisphenoxyphosphorus酰氯（32-92％），以相应的手性二亚磷酸酯。这些化合物都显示出C 2对称并且已被用作铑催化苯乙烯的不对称加氢甲酰化的配体。二亚磷酸酯的催化活性强烈取决于配体的体积。对于庞大的配体，在温和的反应条件下（25–40°C，40 bar合成气），对映体过量最多可达到20％。已发现对支链醛的对映体过量和区域选择性都强烈取决于加氢甲酰化反应条件。
• Ohrui, Hiroshi; Nagihashi, Kazumi; Meguro, Hiroshi, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 11, p. 1721 - 1724
  作者：Ohrui, Hiroshi、Nagihashi, Kazumi、Meguro, Hiroshi

  DOI：——

  日期：——
• PIRRUNG, MICHAEL C.;DUNLAP, STEVEN E.;TRINKS, UWE P., HELV. CHIM. ACTA, 72,(1989) N, C. 1301-1310
  作者：PIRRUNG, MICHAEL C.、DUNLAP, STEVEN E.、TRINKS, UWE P.

  DOI：——

  日期：——
• Ruthenium-Catalyzed Asymmetric <i>N</i>-Demethylative Rearrangement of Isoxazolidines and Its Application in the Asymmetric Total Syntheses of (−)-(1<i>R</i>,3<i>S</i>)-HPA-12 and (+)-(1<i>S</i>,3<i>R</i>)-HPA-12
  作者：Zu-Feng Xiao、Chuan-Zhi Yao、Yan-Biao Kang

  DOI：10.1021/ol503261h

  日期：2014.12.19

  An asymmetric N-demethylative rearrangement of 1,2-isoxazolidines catalyzed by ruthenium is described. Enantioenriched syn-1,3-aminoalcohols as well as cis-1,3-oxazinanes, which are useful building blocks, can be efficiently prepared stereospecifically by this reaction in good yields, via the isoxazolidine intermediates in situ generated from a nitrone bearing a chiral auxiliary and styrenes. This asymmetric reaction was also applied in the asymmetric total syntheses of both (-)-(1R,3S)-HPA-12 and (+)-(1S,3R)-HPA-12.
• Crystalline 4-O-Benzoyl-1,2:5,6-di-O-isopropylidene-D-arabo-3-hexulose. A New Route to Talitol Derivatives
  作者：James M. Sugihara、George U. Yuen

  DOI：10.1021/ja01578a051

  日期：1957.11