(2R,4R,5S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-tetrahydro-furan-2-carbaldehyde | 537007-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,4R,5S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-tetrahydro-furan-2-carbaldehyde
• 英文别名: (2R,4R,5S)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-4-methyloxolane-2-carbaldehyde
• CAS: 537007-55-9
• 化学式: C₁₄H₂₈O₃Si
• 分子量: 272.46
• InChiKey: COJXWUIJSVMHIE-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  18
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4R,5S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-tetrahydro-furan-2-carbaldehyde 在 咪唑 、 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 potassium phosphate buffer 作用下， 以 四氢呋喃 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 21.5h， 生成 (1S,2S)-1-{(2R,4R,5S)-5-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-3-methyl-1-triethylsilyloxy-3-buten-2-ol
  参考文献：
  名称：

  Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments

  摘要：

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00142-x
• 作为产物：
  描述：

  (2'S,3'R,5'R)-2-(5'benzyloxymethyl-3'-methyl-tetrahydrofuran-2'-yl)-ethanol 在 palladium on activated charcoal 咪唑 、 氢气 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 (2R,4R,5S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-tetrahydro-furan-2-carbaldehyde
  参考文献：
  名称：

  Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments

  摘要：

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00142-x

文献信息

• 1-Alkoxyallene as an Effective Precursor for Regio- and Stereocontrolled Allylation Reactions with Aliphatic Aldehydes via Bis-Stannylation
  作者：David R. Williams、Micheal W. Fultz

  DOI：10.1021/ja054201k

  日期：2005.10.1

  Bis-stannylation of 1-(methoxy)methoxyallene yields (E)-(3-(methoxymethoxy)prop-2-ene-1,2-diyl) bis-tributylstannane (2) as a highly reactive allylation reagent. Stereoselective reactions of functionalized stannane 2 with a variety of aldehydes provide good yields of 1,2-diol derivatives. Reactions with alpha-alkoxyaldehydes proceed with chelation-controlled addition to afford efficient constructions

  1-(甲氧基)甲氧基丙二烯的双-甲锡烷基化产生(E)-(3-(甲氧基甲氧基)丙-2-烯-1,2-二基)双-三丁基锡烷(2)作为高反应性烯丙基化试剂。官能化锡烷 2 与各种醛的立体选择性反应提供了良好的 1,2-二醇衍生物产率。与 α-烷氧基醛的反应通过螯合控制加成进行，以在带有三个不同氧（烷氧基和羟基）取代基的立体三联体中有效构建 3,4-反-4,5-syn-关系。提出了机械方面的考虑，核磁共振实验的衍生物支持立体化学分配。包括 X 射线衍射研究。
• Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments
  作者：Takaaki Kubota、Masashi Tsuda、Jun'ichi Kobayashi

  DOI：10.1016/s0040-4020(03)00142-x

  日期：2003.3

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.