(2R,3S)-3,4-O-isopropylidene-2-methyl-1,2,3,4-butanetetrol | 129141-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-3,4-O-isopropylidene-2-methyl-1,2,3,4-butanetetrol
• 英文别名: 2-(2,2-Dimethyl-1,3-dioxolan-4-yl)propane-1,2-diol；(2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propane-1,2-diol
• CAS: 129141-48-6
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: VEVJWYFNIUERBD-POYBYMJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3,4-O-isopropylidene-2-methyl-1,2,3,4-butanetetrol 在 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 19.5h， 生成 (2S,3R)-3,4-Bis-benzyloxy-3-methyl-butane-1,2-diol
  参考文献：
  名称：

  Diastereoselectivity in Organometallic Additions to the Carbonyl Group of Protected Erythrulose Derivatives

  摘要：

  We have investigated a number of nucleophillic additions to L-erythrulose derivatives (4-12) bearing protective O-silyl, O-benzyl, and O-trityl groups in various relative positions. The results are discussed in the frame of chelated vs nonchelated transition states with additional support of previously published theoretical calculations. Sound evidence appears to exist for the formation of alpha-chelates as the key intermediates in nucleophillic additions to these alpha,beta-dioxygenated ketones. Since such evidence is still lacking in the case of beta-chelates, proposals of their intermediacy have been relegated in favor of the more solid Felkin-Anh model, which predicts the same stereochemical result. The behavior of these highly functionalized ketones does not always match that of structurally similar aldehydes.

  DOI：

  10.1021/jo9716744
• 作为产物：
  描述：

  (2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol 在 吡啶 、 chromium trioxide pyridine 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 (2R,3S)-3,4-O-isopropylidene-2-methyl-1,2,3,4-butanetetrol
  参考文献：
  名称：

  格氏试剂对 3,4-O-Isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose 和 1-O-Benzoyl-3,4-O-isopropylidene-L-glycero-2-tetrulose 的非对映选择性加成

  摘要：

  将格氏试剂 (RMgX) 添加到 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose (1) 和 1-O-benzoyl-3,4-O-isopropylidene- 时的非对映选择性L-glycero-2-tetrulose (2) 显着依赖于 R、X、溶剂和反应温度。在 0 °C 的乙醚中 1 和四氢呋喃中的 2 反应中获得了具有中到高非对映选择性的 (2R,3S)-加合物，而在 -78 °C 的乙醚中反应 2 (2S,3S) -加合物是主要产品。(2R)-2-羟甲基-2-壬基环氧乙烷和(2S)-2-羟甲基-2-十四烷基环氧乙烷被合成。

  DOI：

  10.1246/bcsj.65.2814

文献信息

• Nagano, Hajime; Ohno, Mina; Miyame, Yoko, Chemistry Letters, 1990, # 3, p. 463 - 466
  作者：Nagano, Hajime、Ohno, Mina、Miyame, Yoko

  DOI：——

  日期：——
• Diastereoselective synthesis of enantiomeric tertiary alcohols via nucleophilic additions to protected D- and L-erythrulose derivatives
  作者：Miguel Carda、Florenci González、Santiago Rodríguez、J.Alberto Marco

  DOI：10.1016/s0957-4166(00)86047-4

  日期：1992.12

  The diastereoselectivity of the addition of several organometallic reagents to the carbonyl group of protected D- and L-erythrulose derivatives has been investigated. Tertiary alcohols are stereoselectively formed, the diastereomeric ratio being markedly dependent on the reagent type, solvent and temperature.
• Diastereoselectivity in Organometallic Additions to the Carbonyl Group of Protected Erythrulose Derivatives
  作者：J. Alberto Marco、Miguel Carda、Florenci González、Santiago Rodríguez、Encarna Castillo、Juan Murga

  DOI：10.1021/jo9716744

  日期：1998.2.1

  We have investigated a number of nucleophillic additions to L-erythrulose derivatives (4-12) bearing protective O-silyl, O-benzyl, and O-trityl groups in various relative positions. The results are discussed in the frame of chelated vs nonchelated transition states with additional support of previously published theoretical calculations. Sound evidence appears to exist for the formation of alpha-chelates as the key intermediates in nucleophillic additions to these alpha,beta-dioxygenated ketones. Since such evidence is still lacking in the case of beta-chelates, proposals of their intermediacy have been relegated in favor of the more solid Felkin-Anh model, which predicts the same stereochemical result. The behavior of these highly functionalized ketones does not always match that of structurally similar aldehydes.
• Diastereoselective Addition of Grignard Reagents to 3,4-<i>O</i>-Isopropylidene-1-<i>O</i>-triphenylmethyl-L-<i>glycero</i>-2-tetrulose and 1-<i>O</i>-Benzoyl-3,4-<i>O</i>-isopropylidene-L-<i>glycero</i>-2-tetrulose
  作者：Hajime Nagano、Mina Ohno、Yoko Miyamae、Yukie Kuno

  DOI：10.1246/bcsj.65.2814

  日期：1992.10

  Diastereoselectivity in the addition of Grignard reagents (RMgX) to 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose (1) and 1-O-benzoyl-3,4-O-isopropylidene-L-glycero-2-tetrulose (2) depended remarkably on R, X, the solvent, and the reaction temperature. In the reaction of 1 in diethyl ether at 0 °C and 2 in tetrahydrofuran were obtained (2R,3S)-adducts with moderate to high diastereoselectivity

  将格氏试剂 (RMgX) 添加到 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose (1) 和 1-O-benzoyl-3,4-O-isopropylidene- 时的非对映选择性L-glycero-2-tetrulose (2) 显着依赖于 R、X、溶剂和反应温度。在 0 °C 的乙醚中 1 和四氢呋喃中的 2 反应中获得了具有中到高非对映选择性的 (2R,3S)-加合物，而在 -78 °C 的乙醚中反应 2 (2S,3S) -加合物是主要产品。(2R)-2-羟甲基-2-壬基环氧乙烷和(2S)-2-羟甲基-2-十四烷基环氧乙烷被合成。