(E)-3-((2S,3S,4R,5R)-3-Benzyloxy-2-benzyloxymethyl-4-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-acrylic acid methyl ester | 473290-50-5

• 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: (E)-3-((2S,3S,4R,5R)-3-Benzyloxy-2-benzyloxymethyl-4-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-acrylic acid methyl ester
• CAS: 473290-50-5
• 化学式: C₂₄H₂₈O₇
• 分子量: 428.482
• InChiKey: JEMDBKOONZKHQW-JWECKHKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (E)-3-((2S,3S,4R,5R)-3-Benzyloxy-2-benzyloxymethyl-4-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-acrylic acid methyl ester 在 盐酸 、 manganese(IV) oxide 、 正丁基锂 、 草酰氯 、 三氯化硼 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl (2E)-3-{(2S,3S)-3-hydroxy-5-oxo-2-(hydroxymethyl)-4(E)-tetradecylidene[2-(2,3-dihydrofuryl)]}prop-2-enoate
  参考文献：
  名称：

  Conformationally constrained analogues of diacylglycerol (DAG). Part 19: Asymmetric syntheses of (3R)- and (3S)-3-hydroxy-4,4-disubstituted heptono-1,4-lactones as protein kinase C (PK-C) ligands with increased hydrophilicity

  摘要：

  The stereospecific introduction of (R)- and (S)-OH groups at position C-3 of two diacylglycerol gamma-lactones (DAG-lactones) previously identified as strong protein kinase C (PK-C) ligands is presented. The compounds were designed to investigate whether the extra OH group in a specific orientation could establish an additional hydrogen bond with the C1 domain of PK-C, thus providing a DAG analogue with reduced lipophilicity. The OH groups were introduced following two different diastereoselective multistep syntheses starting from diacetone-D-glucose. The PK-C binding affinities for the new compounds were weaker in comparison to those of the parent compounds, suggesting that the extra OH does not engage efficiently in hydrogen bonding at the receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00477-5
• 作为产物：
  描述：

  (3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (E)-3-((2S,3S,4R,5R)-3-Benzyloxy-2-benzyloxymethyl-4-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-acrylic acid methyl ester
  参考文献：
  名称：

  Conformationally constrained analogues of diacylglycerol (DAG). Part 19: Asymmetric syntheses of (3R)- and (3S)-3-hydroxy-4,4-disubstituted heptono-1,4-lactones as protein kinase C (PK-C) ligands with increased hydrophilicity

  摘要：

  The stereospecific introduction of (R)- and (S)-OH groups at position C-3 of two diacylglycerol gamma-lactones (DAG-lactones) previously identified as strong protein kinase C (PK-C) ligands is presented. The compounds were designed to investigate whether the extra OH group in a specific orientation could establish an additional hydrogen bond with the C1 domain of PK-C, thus providing a DAG analogue with reduced lipophilicity. The OH groups were introduced following two different diastereoselective multistep syntheses starting from diacetone-D-glucose. The PK-C binding affinities for the new compounds were weaker in comparison to those of the parent compounds, suggesting that the extra OH does not engage efficiently in hydrogen bonding at the receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00477-5