(2R,3'S,4aS,5'R,6S,8aR)-3',4a-dimethyl-5'-(phenylmethoxymethyl)spiro[3,4,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2,2'-oxolane]-6-carbaldehyde | 837376-80-4

• 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: (2R,3'S,4aS,5'R,6S,8aR)-3',4a-dimethyl-5'-(phenylmethoxymethyl)spiro[3,4,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2,2'-oxolane]-6-carbaldehyde
• CAS: 837376-80-4
• 化学式: C₂₂H₃₀O₅
• 分子量: 374.477
• InChiKey: RQIBRGSCSJHUQM-ZTRCUUGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3'S,4aS,5'R,6S,8aR)-3',4a-dimethyl-5'-(phenylmethoxymethyl)spiro[3,4,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2,2'-oxolane]-6-carbaldehyde 在 甲基磺酰胺 、 AD-mix-β 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 29.25h， 生成 tert-butyl (2E,4E,6R,7S)-7-[(2R,3'S,4aS,5'R,6S,8aR)-3',4a-dimethyl-5'-(phenylmethoxymethyl)spiro[3,4,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2,2'-oxolane]-6-yl]-6,7-dihydroxy-3,4-dimethylhepta-2,4-dienoate
  参考文献：
  名称：

  Diversity-Oriented Synthesis of Polyketide Natural Products via Iterative Chemo- and Stereoselective Functionalization of Polyenoates:  Development of a Unified Approach for the C(1−19) Segments of Lituarines A−C

  摘要：

  A unified, stereocontrolled synthesis of the C(1-19) segments of the lituarines A-C (1-3) has been achieved, highlighted by application of an iterative chemo- and stereoselective trienoate functionalization protocol, a strategy that holds considerable promise for the diversity oriented synthesis of polyketides.

  DOI：

  10.1021/ol047792c
• 作为产物：
  描述：

  在 pyridine-SO3 complex 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3'S,4aS,5'R,6S,8aR)-3',4a-dimethyl-5'-(phenylmethoxymethyl)spiro[3,4,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2,2'-oxolane]-6-carbaldehyde
  参考文献：
  名称：

  Diversity-Oriented Synthesis of Polyketide Natural Products via Iterative Chemo- and Stereoselective Functionalization of Polyenoates:  Development of a Unified Approach for the C(1−19) Segments of Lituarines A−C

  摘要：

  A unified, stereocontrolled synthesis of the C(1-19) segments of the lituarines A-C (1-3) has been achieved, highlighted by application of an iterative chemo- and stereoselective trienoate functionalization protocol, a strategy that holds considerable promise for the diversity oriented synthesis of polyketides.

  DOI：

  10.1021/ol047792c

文献信息

• Diversity-Oriented Synthesis of Polyketide Natural Products via Iterative Chemo- and Stereoselective Functionalization of Polyenoates:  Development of a Unified Approach for the C(1−19) Segments of Lituarines A−C
  作者：Amos B. Smith、Shawn P. Walsh、Michael Frohn、Matthew O. Duffey

  DOI：10.1021/ol047792c

  日期：2005.1.1

  A unified, stereocontrolled synthesis of the C(1-19) segments of the lituarines A-C (1-3) has been achieved, highlighted by application of an iterative chemo- and stereoselective trienoate functionalization protocol, a strategy that holds considerable promise for the diversity oriented synthesis of polyketides.