1.2;3.4-Di-O-isopropyliden-D-threit | 166375-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1.2;3.4-Di-O-isopropyliden-D-threit
• 英文别名: (4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane
• CAS: 166375-53-7
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: RPUCAUHQAMMFPS-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1.2;3.4-Di-O-isopropyliden-D-threit 在 (三甲基硅基)甲基氯化镁 作用下， 以 苯 为溶剂， 以67%的产率得到(2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol
  参考文献：
  名称：

  Selective deprotection of an acetal group in monosaccharide derivatives and related compounds using Me3SiCH2MgCl

  摘要：

  用Me3SiCH2MgCl处理相邻二醇的缩醛可以有选择性地释放出相应的二醇；配位作用被用来合理化这种选择性。

  DOI：

  10.1039/cc9960000327

文献信息

• Chelation-Assisted Regioselective C−O Bond Cleavage Reactions of Acetals by Grignard Reagents. A General Procedure for the Regioselective Synthesis of Protected Polyols Having One Free Hydroxy Group
  作者：Wen-Lung Cheng、Yeng-Jeng Shaw、Sue-Min Yeh、Puthuparampil P. Kanakamma、Yu-Huey Chen、Chuo Chen、Jia-Cheng Shieu、Shaang-Jyh Yiin、Gene-Hsiang Lee、Yu Wang、Tien-Yau Luh

  DOI：10.1021/jo981579a

  日期：1999.1.1

  Acetals containing a neighboring heteroatom react with the Grignard reagent in aromatic hydrocarbon solvents regioselectively. The auxiliary moiety can be hydroxy, alkoxy, or amino but not sulfur. Chelation plays a key role in directing the regioselectivity of this ring opening reaction. The reactions of acetonide derivatives of monosaccharides under these conditions afford the corresponding products having only one free hydroxy group at the specific position. Fully protected mannosamine derivative is prepared in good yield. The stereochemistry of the carbon center where auxiliary group is attached can be either syn or anti to the acetal oxygen moiety where cleavage of the C-O bond occurs. However, difference in reactivity has been found in the reaction of tris-acetonide of sorbitol with MeMgI. Regioselective ring opening of the acetal group at the anomeric carbon generates a hemiacetal which underwent further nucleophilic addition to furnish the corresponding alcohol stereoselectively.
• Highly Diastereoselective Ring-Opening Reactions of Chiral Acetals with Secondary or Sterically Hindered Grignard Reagents
  作者：Tien-Min Yuan、Sue-Min Yeh、Yu-Tsai Hsieh、Tien-Yau Luh

  DOI：10.1021/jo00105a041

  日期：1994.12

  There has been an increasing interest in the stereoselective ring opening of acetals by means of nucleophiles.(1-4) Most of these approaches involve the preferential complex formation of acetals with a Lewis acid and subsequent invertive substitution by nucleophiles (Scheme 1).(2) The retentive ring cleavage of acetals has been investigated only briefly, mostly related to the reductive ring opening with metal hydrides.(3,4) Recently, Yamamoto and his co-workers reported the highly diastereoselective retentive alkylation of chiral acetals using novel organoaluminum reagents.(4) However, only methyl- or primary alkylaluminum reagents can be used. We now wish to describe our investigations on the highly diastereoselective reactions of secondary or sterically bulky Grignard reagents with chiral acetals prepared from aldehydes and tunable chiral diols.
• Selective deprotection of an acetal group in monosaccharide derivatives and related compounds using Me3SiCH2MgCl
  作者：Yu-Huei Chen、Yueh-Ting Tseng、Tien-Yau Luh

  DOI：10.1039/cc9960000327

  日期：——

  Treatment of an acetal of a contiguous diol with Me3SiCH2MgCl liberates the corresponding diol regioselectively; chelation is used to rationalize the selectively.

  用Me3SiCH2MgCl处理相邻二醇的缩醛可以有选择性地释放出相应的二醇；配位作用被用来合理化这种选择性。