1-[(2S,6R)-6-(2-hydroxyethyl)oxan-2-yl]propan-2-one | 910330-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-[(2S,6R)-6-(2-hydroxyethyl)oxan-2-yl]propan-2-one
• CAS: 910330-81-3
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: WVUKEXWIZHQOQY-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(2S,6R)-6-(2-hydroxyethyl)oxan-2-yl]propan-2-one 在 吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-[(2R,6S)-6-(2-trimethylsilyloxyprop-2-enyl)oxan-2-yl]ethyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  ASSEMBLY OF THE SOUTHERN MACROCYCLIC HALF OF (+)-SPIRASTRELLOLIDE A THROUGH CYCLIC ACETAL TETHERED RING-CLOSING METATHESIS AND 1,3-ANTI-MUKAIYAMA-ALDOL

  摘要：

  We describe herein details of our efforts in syntheses of A-ring and BC-ring of (+)-spirastrellolide A. While the former would constitute a facile 12-step synthetic endeavor starting from 1,5-pentanediol, the latter would showcase a cyclic acetal-tethered ring-closing metathesis [RCM] method that was developed in our lab for de novo synthesis of spiroketals. Constructing the entire Southern Half of the macrocycle would require 1,3-anti-Mukaiyama aldol addition for connecting A-ring and BC-ring specifically at C10 and C11, thereby culminating a 17-step approach for the Southern Macrocyclic Half linearly from (+)-2,3-(O)-iso-propylidene-L-threitol. Also discussed here is the possibility of pursuing a more convergent approach toward the assembly of the Southern Half through first connecting A-ring and C-ring via acetal formation that would first link together the free C13-OH with C17 at the spiro-BC-ring junction. An ensuing application of our cyclic acetal-tethered RCM strategy to close B-ring would adopt this cyclic acetal intermediate.

  DOI：

  10.3987/com-12-s(n)54
• 作为产物：
  描述：

  7-benzyloxy-hept-2-enoic acid ethyl ester 在 palladium on activated charcoal titanium(IV) isopropylate 、 叔丁基过氧化氢 、 (-)-diisopropyl tartrate 、 pyridine-SO3 complex 、 氢气 、 二异丁基氢化铝 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 红铝 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 生成 1-[(2S,6R)-6-(2-hydroxyethyl)oxan-2-yl]propan-2-one
  参考文献：
  名称：

  Synthesis of the C1–C16 fragment of spirastrellolide A

  摘要：

  Synthesis of the Cl-C16 fragment of spirastrellolide A is described here featuring Sharpless asymmetric epoxidation, an acid promoted O-1,4-addition, and Mukaiyama 1,3-anti-aldol. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.067

文献信息

• ASSEMBLY OF THE SOUTHERN MACROCYCLIC HALF OF (+)-SPIRASTRELLOLIDE A THROUGH CYCLIC ACETAL TETHERED RING-CLOSING METATHESIS AND 1,3-ANTI-MUKAIYAMA-ALDOL
  作者：Richard P. Hsung、Yu Tang、Jin-Haek Yang、Jia Liu、Chao-Chao Wang、Ming-Can Lv、Yi-Biao Wu、Xue-Liang Yu、Changhong Ko

  DOI：10.3987/com-12-s(n)54

  日期：——

  We describe herein details of our efforts in syntheses of A-ring and BC-ring of (+)-spirastrellolide A. While the former would constitute a facile 12-step synthetic endeavor starting from 1,5-pentanediol, the latter would showcase a cyclic acetal-tethered ring-closing metathesis [RCM] method that was developed in our lab for de novo synthesis of spiroketals. Constructing the entire Southern Half of the macrocycle would require 1,3-anti-Mukaiyama aldol addition for connecting A-ring and BC-ring specifically at C10 and C11, thereby culminating a 17-step approach for the Southern Macrocyclic Half linearly from (+)-2,3-(O)-iso-propylidene-L-threitol. Also discussed here is the possibility of pursuing a more convergent approach toward the assembly of the Southern Half through first connecting A-ring and C-ring via acetal formation that would first link together the free C13-OH with C17 at the spiro-BC-ring junction. An ensuing application of our cyclic acetal-tethered RCM strategy to close B-ring would adopt this cyclic acetal intermediate.
• Synthesis of the C1–C16 fragment of spirastrellolide A
  作者：Jia Liu、Jin Haek Yang、Changhong Ko、Richard P. Hsung

  DOI：10.1016/j.tetlet.2006.06.067

  日期：2006.8

  Synthesis of the Cl-C16 fragment of spirastrellolide A is described here featuring Sharpless asymmetric epoxidation, an acid promoted O-1,4-addition, and Mukaiyama 1,3-anti-aldol. (c) 2006 Elsevier Ltd. All rights reserved.