(Z)-3-C-acetoxymethyl-1,2,3,4,5-pentadeoxy-6,7:8,9-di-O-isopropylidene-β-D-manno-dec-4-ene-6-ulo-6,10-pyranose | 223567-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-C-acetoxymethyl-1,2,3,4,5-pentadeoxy-6,7:8,9-di-O-isopropylidene-β-D-manno-dec-4-ene-6-ulo-6,10-pyranose
• 英文别名: [(Z,2R)-2-ethyl-4-[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]but-3-enyl] acetate
• CAS: 223567-91-7
• 化学式: C₁₉H₃₀O₇
• 分子量: 370.443
• InChiKey: RGSSGSGYMUDMQD-NNONHNINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-3-C-acetoxymethyl-1,2,3,4,5-pentadeoxy-6,7:8,9-di-O-isopropylidene-β-D-manno-dec-4-ene-6-ulo-6,10-pyranose 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、517.11 kPa 条件下， 反应 48.0h， 生成 1,2,3,4,5-pentadeoxy-3C-hydroxymethyl-6,7:8,9-di-O-isopropylidene-β-D-manno-dec-6-ulo-6,10-pyranose
  参考文献：
  名称：

  Chiral building-blocks by chemoenzymatic desymmetrization of 2-ethyl-1,3-propanediol for the preparation of biologically active natural products

  摘要：

  2-Ethyl-1,3-propanediol 1 and its related di-O-acetate 2 were desymmetrized by partial chemoenzymatic acetylation and deacetylation, by Pseudomonas fluorescens lipase (Amano P.; PFL), to (R)-1-O-acetyl-2-ethyl-1,3-propanediol 3. On treatment of 3 with I-2/Ph3P/imidazole the related (S)-1-O-acetyl-2-ethyl-3-iodopropanol 4 was obtained and transformed into the corresponding triphenylphosphonium salt 5. Reaction of [(S)-3-acetoxy-2-ethylpropylidene] triphenylphosphorane 6, prepared from 5, with 2,3 :4,5-di-O-isopropylidene-beta-D-arabino-hexos-2-ulopyranose 7 gave (2)-3-C-acetoxymethyl-1,2,3,4,5-pentadeoxy-6,7:8,9-di-O-isopropylidene-beta-D-manno-dec-4-ene-6-ulo-6,10-pyranose 8 which was hydrogenated to 9 and subsequently deacylated to 10. Treatment of 10 with Me2CO/H+ caused a rearrangement to (3R,4R,5S,6R,9R)-9-ethyl-5-hydroxy-3,4-isopropylidenedioxy-1,7-dioxaspiro[5.5]undecane 11, which closely matched the skeleton of the talaromycins. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00020-8
• 作为产物：
  描述：

  <(S)-3-acetoxy-2-ethylpropyl>triphenylphosphonium iodide 在 potassium tert-butylate 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 0.5h， 生成 (Z)-3-C-acetoxymethyl-1,2,3,4,5-pentadeoxy-6,7:8,9-di-O-isopropylidene-β-D-manno-dec-4-ene-6-ulo-6,10-pyranose
  参考文献：
  名称：

  Chiral building-blocks by chemoenzymatic desymmetrization of 2-ethyl-1,3-propanediol for the preparation of biologically active natural products

  摘要：

  2-Ethyl-1,3-propanediol 1 and its related di-O-acetate 2 were desymmetrized by partial chemoenzymatic acetylation and deacetylation, by Pseudomonas fluorescens lipase (Amano P.; PFL), to (R)-1-O-acetyl-2-ethyl-1,3-propanediol 3. On treatment of 3 with I-2/Ph3P/imidazole the related (S)-1-O-acetyl-2-ethyl-3-iodopropanol 4 was obtained and transformed into the corresponding triphenylphosphonium salt 5. Reaction of [(S)-3-acetoxy-2-ethylpropylidene] triphenylphosphorane 6, prepared from 5, with 2,3 :4,5-di-O-isopropylidene-beta-D-arabino-hexos-2-ulopyranose 7 gave (2)-3-C-acetoxymethyl-1,2,3,4,5-pentadeoxy-6,7:8,9-di-O-isopropylidene-beta-D-manno-dec-4-ene-6-ulo-6,10-pyranose 8 which was hydrogenated to 9 and subsequently deacylated to 10. Treatment of 10 with Me2CO/H+ caused a rearrangement to (3R,4R,5S,6R,9R)-9-ethyl-5-hydroxy-3,4-isopropylidenedioxy-1,7-dioxaspiro[5.5]undecane 11, which closely matched the skeleton of the talaromycins. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00020-8