2,3,4-tri-O-methyl-β-D-xylopyranosyl trichloroacetimidate | 884338-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-methyl-β-D-xylopyranosyl trichloroacetimidate
• 英文别名: 2,2,2-trichloroacetimidic acid 3,4,5-trimethoxytetrahydropyran-2-yl ester；[(2S,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl] 2,2,2-trichloroethanimidate
• CAS: 884338-38-9
• 化学式: C₁₀H₁₆Cl₃NO₅
• 分子量: 336.6
• InChiKey: YYCNOVUFGSPZAZ-CWKFCGSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-methyl-β-D-xylopyranosyl trichloroacetimidate 、 (1S,5S,7S,9S,10R,11S,15S,17S,19S,20R)-9,19-Dihydroxy-10,20-dimethyl-5,15-bis-((1S,2S)-2-methyl-cyclopropyl)-4,14,21,22-tetraoxa-tricyclo[15.3.1.1^7,11]docosane-3,13-dione 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以21%的产率得到clavosolide A
  参考文献：
  名称：

  直接合成clavosolides的研究：clavosolide A异构体的合成

  摘要：

  clavosolide A的总合成采用自由基介导的途径来构建其取代的四氢吡喃单元，通过Yamaguchi反应来构建乙交酯糖苷配基，而Schmidt方法用于最后的糖苷化步骤，表明所报道的结构是天然产物的异构体。

  DOI：

  10.1016/j.tetlet.2006.01.130
• 作为产物：
  描述：

  (3R,4S,5R)-2,3,4,5-tetramethoxytetrahydro-2H-pyran 在 盐酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 2,3,4-tri-O-methyl-β-D-xylopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Total Synthesis, Structural Revision, and Absolute Configuration of (+)-Clavosolide A

  摘要：

  Enantioselective synthesis of 3, a revised structure for clavosolide A, was completed. Both H-1 and C-13 NMR spectra of the natural and synthetic compounds were identical, and optical rotation measurements identified the absolute configuration of the natural clavosolide A as the enantiomer of 3.

  DOI：

  10.1021/ol052851n

文献信息

• Enantioselective Total Synthesis of (-)-Clavosolide A and B
  作者：Jung-Beom Son、Si-Nae Kim、Na-Yeong Kim、Min-Ho Hwang、Won-Sun Lee、Duck-Hyung Lee

  DOI：10.5012/bkcs.2010.31.03.653

  日期：2010.3.20

  Enantioselective total synthesis of (-)-clavosolide A and B was reported in full including the synthesis of proposed structure of (-)-clavosoldie A (1), revised structure of (-)-clavosoldie A (5), and revised structure of (-)-clavosoldie B (6). The relative and absolute stereochemistries of the natural products were confirmed unambiguously by comparing the optical rotation values and $^1H$ and $^13}C$ NMR spectra of them.

  完全报道了(-)-clavosolide A和B的对映选择性全合成，包括所提出的(-)-clavosolide A (1)结构的合成、修订后的(-)-clavosolide A (5)结构的合成以及修订后的(-)-clavosolide B (6)结构的合成。通过比较其旋光值和$^1H$及$^13}C$核磁共振谱，明确证实了这些天然产物的相对和绝对立体化学。
• Total Synthesis, Structural Revision, and Absolute Configuration of (+)-Clavosolide A
  作者：Jung Beom Son、Si Nae Kim、Na Yeong Kim、Duck Hyung Lee

  DOI：10.1021/ol052851n

  日期：2006.2.1

  Enantioselective synthesis of 3, a revised structure for clavosolide A, was completed. Both H-1 and C-13 NMR spectra of the natural and synthetic compounds were identical, and optical rotation measurements identified the absolute configuration of the natural clavosolide A as the enantiomer of 3.
• Studies directed towards the total synthesis of clavosolides: synthesis of an isomer of clavosolide A
  作者：Tushar Kanti Chakraborty、Vakiti Ramkrishna Reddy

  DOI：10.1016/j.tetlet.2006.01.130

  日期：2006.3

  The total synthesis of clavosolide A, employing a radical-mediated route to build its substituted tetrahydropyran unit, a Yamaguchi reaction to construct the diolide aglycon and the Schmidt method for the final glycosidation step, revealed that the reported structure is an isomer of the natural product.

  clavosolide A的总合成采用自由基介导的途径来构建其取代的四氢吡喃单元，通过Yamaguchi反应来构建乙交酯糖苷配基，而Schmidt方法用于最后的糖苷化步骤，表明所报道的结构是天然产物的异构体。