(4S,5R,6S)-4,5-Diacetoxy-6-((2R,3R,4R,5S,6S)-2,4,5-triacetoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester | 148967-08-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5R,6S)-4,5-Diacetoxy-6-((2R,3R,4R,5S,6S)-2,4,5-triacetoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3R,4S)-3,4-diacetyloxy-2-[(2R,3R,4R,5S,6S)-2,4,5-triacetyloxy-6-methyloxan-3-yl]oxy-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 148967-08-2
• 化学式: C₂₃H₃₀O₁₅
• 分子量: 546.482
• InChiKey: HDOPPEJVKGTALN-RXPQIHSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-4,5-Diacetoxy-6-((2R,3R,4R,5S,6S)-2,4,5-triacetoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.08h， 以52 mg的产率得到lepidimoide
  参考文献：
  名称：

  A convenient synthesis of lepidimoide from okra mucilage and its growth-promoting activity in hypocotyls

  摘要：

  The total synthesis of the unsaturated disaccharide, lepidimoide 4-deoxy-beta-L-threo-hex-4-enopyranuronosyl-(1 --> 2)-L-rhamnopyranose sodium salt, has been carried out from D-glucose and L-rhamnose (Tetrahedron Lett. 1993, 34, 2653), but the process is very long and complicated. A method for more easily producing this compound and in large quantities is necessary for further research. We have succeeded in conveniently synthesizing lepidimoide from okra (Hibiscus esculentus L.) fruit mucilage. At the same time, the isomer (epi-lepidimoide) was obtained as a byproduct. The structure was determined as the 4-deoxy-beta-L-threo-hex-4-enopyranuronosyl-(1 --> 2)-6-deoxy-L-glucopyranose sodium salt by spectral analysis. We found that lepidimoide easily epimerized to epi-lepidimoide in alkaline media. Both lepidimoide and epi-lepidimoide exhibited the same high activity in the cockscomb hypocotyls elongation test. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.10.003
• 作为产物：
  描述：

  (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((3R,4R,5S,6S)-2,4,5-triacetoxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 为溶剂， 以43%的产率得到(4S,5R,6S)-4,5-Diacetoxy-6-((2R,3R,4R,5S,6S)-2,4,5-triacetoxy-6-methyl-tetrahydro-pyran-3-yloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  从萌发的水芹种子的粘液中合成高效的化感物质鳞翅类化合物的合成和绝对构型

  摘要：

  由D-葡萄糖和α-L-鼠李糖合成了1，2-顺式联结的双糖莱皮莫胺（1），用于确定绝对构型。

  DOI：

  10.1016/s0040-4039(00)77648-9