1-[(2R,3S,6R)-tetrahydro-6-methyl-3-(phenylmethoxy)-2H-pyran-2-yl]-2-propanone | 265656-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(2R,3S,6R)-tetrahydro-6-methyl-3-(phenylmethoxy)-2H-pyran-2-yl]-2-propanone
• 英文别名: 1-[(2R,3S,6R)-6-methyl-3-phenylmethoxyoxan-2-yl]propan-2-one
• CAS: 265656-41-5
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: JVCNCNXUAXUTQC-VNQPRFMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  1-[(2R,3S,6R)-tetrahydro-6-methyl-3-(phenylmethoxy)-2H-pyran-2-yl]-2-propanone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 5.0h， 以94%的产率得到1-[(2R,3S,6R)-tetrahydro-3-hydroxy-6-methyl-2H-pyran-2-yl]-2-propanone
  参考文献：
  名称：

  Synthesis of (+)-decarestrictine L

  摘要：

  A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl-D-glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00126-5
• 作为产物：
  描述：

  2,6-anhydro-1,3,4-trideoxy-4-O-(phenylmethyl)-D-arabino-heptitol 6-methylbenzenesulfonate 在 氢氧化钾 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 1-[(2R,3S,6R)-tetrahydro-6-methyl-3-(phenylmethoxy)-2H-pyran-2-yl]-2-propanone
  参考文献：
  名称：

  Synthesis of (+)-decarestrictine L

  摘要：

  A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl-D-glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00126-5

文献信息

• Enantioselective Synthesis of (+)-Decarestrictine L from (2E,5E)-Dibenzyloxy-2,5-heptadien-4-ol
  作者：Susumi Hatakeyama、Tomoyuki Esumi、Rieko Kimura、Masako Mori、Yoshiharu Iwabuchi、Hiroshi Irie

  DOI：10.3987/com-99-s60

  日期：——
• Synthesis of (+)-decarestrictine L
  作者：Julie M. Lukesh、William A. Donaldson

  DOI：10.1016/s0957-4166(03)00126-5

  日期：2003.3

  A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl-D-glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.