(2R,3S)-6-异丙氧基-3-甲基-3,6-二氢-2H-吡喃-2-甲醛 | 217640-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: (2R,3S)-6-异丙氧基-3-甲基-3,6-二氢-2H-吡喃-2-甲醛
• 英文名称: (2R,3S)-3-methyl-6-propan-2-yloxy-3,6-dihydro-2H-pyran-2-carbaldehyde
• CAS: 217640-00-1
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: OITTXKLFODQRBU-XMCUXHSSSA-N

物化性质

• 沸点：
  259.0±40.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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,3S)-6-异丙氧基-3-甲基-3,6-二氢-2H-吡喃-2-甲醛 在 二氯甲烷 、 Dowex HCR-W₂ 、 dimsyl lithium 、 silver carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 叔丁醇 作用下， 以 水 、 丙酮 、 甲苯 、 苯 为溶剂， 生成 (2S,3S)-2-[(1E,3Z,5R)-3-ethyl-7-hydroxy-5-methylhepta-1,3-dienyl]-3-methyl-2,3-dihydropyran-6-one
  参考文献：
  名称：

  Absolute stereostructure and total synthesis of leptomycin B

  摘要：

  The absolute stereostructure of leptomycin B, an antitumor antibiotic and inhibitor of nuclear protein export, was firstly presumed as 1 having 4S, 5R, 10R, 16R, 18S, 19R, 20S on the basis of NMR comparison with callystatin A (2) and then 1 was asymmetrically synthesized. The synthesized leptomycin B (I) was found identical with the authentic sample in HPLC and CD comparison as well as in other respects. This structural elucidation of the absolute stereostructure and total synthesis are the first example;among the leptomycin family as Streptomyces metabolites. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01809-7
• 作为产物：
  描述：

  (4R)-4-[(2S)-4,4-dibromobut-3-en-2-yl]-2,2-dimethyl-1,3-dioxolane 在 Lindlar's catalyst 正丁基锂 、 草酰氯 、 Dowex 50W X₈ 、 四丁基氟化铵 、 氢气 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 43.0h， 生成 (2R,3S)-6-异丙氧基-3-甲基-3,6-二氢-2H-吡喃-2-甲醛
  参考文献：
  名称：

  First Total Synthesis of the Antitumor Compound (−)-Kazusamycin A and Absolute Structure Determination

  摘要：

  The first total synthesis of kazusamycin A, a potent antitumor compound from an actinomycete, has been achieved, and its absolute structure was determined. Paterson's stereoselective aldol reaction was successfully applied to construct the contiguous chiral centers by using an originally designed optically active 2-acyl-1,3-propanediol derivative.

  DOI：

  10.1021/ol049219z

文献信息

• Absolute stereostructure and total synthesis of leptomycin B
  作者：Motomasa Kobayashi、Weiqi Wang、Yasuhiro Tsutsui、Masanori Sugimoto、Nobutoshi Murakami

  DOI：10.1016/s0040-4039(98)01809-7

  日期：1998.11

  The absolute stereostructure of leptomycin B, an antitumor antibiotic and inhibitor of nuclear protein export, was firstly presumed as 1 having 4S, 5R, 10R, 16R, 18S, 19R, 20S on the basis of NMR comparison with callystatin A (2) and then 1 was asymmetrically synthesized. The synthesized leptomycin B (I) was found identical with the authentic sample in HPLC and CD comparison as well as in other respects. This structural elucidation of the absolute stereostructure and total synthesis are the first example;among the leptomycin family as Streptomyces metabolites. (C) 1998 Elsevier Science Ltd. All rights reserved.
• First Total Synthesis of the Antitumor Compound (−)-Kazusamycin A and Absolute Structure Determination
  作者：Noriyoshi Arai、Noriko Chikaraishi、Satoshi Omura、Isao Kuwajima

  DOI：10.1021/ol049219z

  日期：2004.8.1

  The first total synthesis of kazusamycin A, a potent antitumor compound from an actinomycete, has been achieved, and its absolute structure was determined. Paterson's stereoselective aldol reaction was successfully applied to construct the contiguous chiral centers by using an originally designed optically active 2-acyl-1,3-propanediol derivative.