(2R,3R)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol | 102389-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol
• 英文别名: (1S)-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(4-methoxyphenyl)methanol；(R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(4-methoxyphenyl)methanol；(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(4-methoxyphenyl)methanol
• CAS: 102389-96-8
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: XXAMFTRQXVCAFM-VXGBXAGGSA-N

物化性质

• 熔点：
  41-42 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  355.3±32.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol 在 sodium hydride 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 7.5h， 生成 2-((R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(4-methoxyphenyl)methoxy)-1-phenylethanone
  参考文献：
  名称：

  手性苄基作为合成光学活性 1,2-二醇和 (+)-Frontalin 的手性助剂和保护基团

  摘要：

  格氏试剂与手性 α-苄氧基酮的螯合控制的不对称亲核加成通过 1,4-不对称诱导产生具有高非对映选择性（高达 96% de）的相应醇。手性苄基用作手性助剂和保护基团，用于合成光学活性 1,2-二醇和 (+)-frontalin。

  DOI：

  10.1055/s-0033-1340163
• 作为产物：
  描述：

  ((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(4-methoxy-phenyl)-methanone 生成 (2R,3R)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol
  参考文献：
  名称：

  CHIKASHITA, HIDENORI;NIKAYA, TOSHIKI;UEMURA, HIROMITSU;ITOH, KAZUYOSHI, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 2121-2123

  摘要：

  DOI：

文献信息

• Synthesis of the rarely obtained syn-adducts in the reaction of organocopper compounds with 2,3-O-isopropylideneglyceraldehyde. Preparation of optically active epoxy alcohols
  作者：Fumie Sato、Yuichi Kobayashi、Osamu Takahashi、Tsunehisa Chiba、Yoshiyuki Takeda、Masato Kusakabe

  DOI：10.1039/c39850001636

  日期：——

  Organocopper compounds, prepared from Grignard reagents and copper(I) iodide in tetrahydrofuran-dimethyl sulphide, react with 2,3-O-isopropylideneglyceraldehyde highly stereoselectively (>10:1) affording the rarely obtained syn-addition products which can be readily converted into optically active epoxy alcohols, useful intermediates in organic synthesis.

  由格氏试剂和碘化亚铜（I）在四氢呋喃-二甲基硫醚中制备的有机铜化合物与2,3- O-异亚丙基甘油醛高度立体选择性（> 10：1）反应，提供了很少获得的合成加成产物，可以轻松地将其转化为旋光性环氧醇，在有机合成中有用的中间体。
• Stereoselective<i>syn</i>-Reduction of (<i>R</i>)-4-Acyl-2,2-dimethyl-1,3-dioxolanes with Metal Hydride Reagents
  作者：Hidenori Chikashita、Toshiki Nikaya、Hiromitsu Uemura、Kazuyoshi Itoh

  DOI：10.1246/bcsj.62.2121

  日期：1989.6

  Lithium tri-s-butylborohydride and lithium aluminum hydride were found to be efficient reducing agents for the stereoselective preparation of syn-glycerol derivatives from (R)-4-acyl-2,2-dimethyl-1,3-dioxolanes. The scope and limitation of the stereoselective L-Selectride reduction of (R)-4-acyl-2,2-dimethyl-1,3-dioxolanes were also described.

  发现三叔丁基硼氢化锂和氢化铝锂是从 (R)-4-酰基-2,2-二甲基-1,3-二氧戊环立体选择性制备合成甘油衍生物的有效还原剂。还描述了 (R)-4-酰基-2,2-二甲基-1,3-二氧戊环的立体选择性 L-Selectride 还原的范围和限制。
• Stereoselective synthesis of (−)-centrolobine
  作者：Zunhua Yang、Hee-Doo Kim

  DOI：10.1016/j.tetasy.2013.12.019

  日期：2014.2

  The stereoselective synthesis of (−)-centrolobine has been accomplished starting from d-glyceraldehyde acetonide by a combination of chelation-controlled diastereoselective alkylation and ring-closing metathesis. A high degree of 1,3-asymmetric induction has been realized in an ether system.

  （d）-甘油醛丙酮化物是通过螯合控制的非对映选择性烷基化和闭环易位的结合而完成（-）-中心叶氨酸的立体选择性合成的。在醚体系中已经实现了高度的1，3-不对称感应。
• Bidentate chelation-controlled asymmetric synthesis of α-hydroxy esters based on the glycolate enolate alkylation
  作者：Ju Eun Jung、Hyunsoon Ho、Hee-Doo Kim

  DOI：10.1016/s0040-4039(00)00031-9

  日期：2000.3

  (S)-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl](4-methoxyphenyl)methanol (4b) has been synthesized and evaluated as a chiral auxiliary for the asymmetric synthesis of α-hydroxy esters based on bidentate chelation-controlled alkylation of glycolate enolate.

  （S）-[（（4 R）-2,2-二甲基-1,3-二氧戊环-4-基]（4-甲氧基苯基）甲醇（4b）已合成并评估为手性助剂，用于α的不对称合成-羟基酸酯基于乙醇酸酯烯酸酯的双齿螯合控制烷基化。
• A Novel Stereoselective Total Synthesis of (+)‐5‐<i>epi</i>‐Cytoxazone
  作者：Navath Raghavendra Swamy、Pendem Krishnaiah、Natala Srinivasa Reddy、Yenamandra Venkateswarlu

  DOI：10.1081/car-200030048

  日期：2004.12.29

  Stereoselective synthesis of a potent cytokine modulator cytoxazone isomer has been achieved from 2,3-O-isopropylidene D-glyceraldehyde involving Grignard reaction, subsequent formation of an azide followed by reduction to the aminodiol, and finally cyclization of the N-Boc diol.