(2R,3S)-2-(3-benzyloxyphenyl)-5,7-dibenzyloxy-chroman-3-ol | 1607010-88-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2R,3S)-2-(3-benzyloxyphenyl)-5,7-dibenzyloxy-chroman-3-ol
• CAS: 1607010-88-7
• 化学式: C₃₆H₃₂O₅
• 分子量: 544.647
• InChiKey: DSADSFXCLDFPSF-MSEJLTFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.46
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-(3-benzyloxyphenyl)-5,7-dibenzyloxy-chroman-3-ol 在 L-Selectride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (2R,3R)-3'-benzyloxy-4'',6''-dibenzyloxyflavan
  参考文献：
  名称：

  Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance

  摘要：

  The high-yielding synthesis of enantiomerically pure epicatechin gallate analogues where the A and/or B-ring hydroxylation is reduced or altered has been achieved by optimising routes to the catechin stereochemistry. The B-ring analogues were synthesised by using an electrophilic ring closure onto an enantiomerically enriched epoxide as a key step. The A and B-ring hydroxyl-deleted analogues were synthesised through a Mitsunobu cyclisation. For the B-ring analogues, the anti- (catechin) stereochemistry was converted to the syn- (epicatechin) stereochemistry by a known oxidation/reduction protocol. Absolute stereochemistry was derived from either a Sharpless epoxidation or asymmetric dihydroxylation. (C) 2014 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.052
• 作为产物：
  描述：

  ((2S,3S)-3-(3-benzyloxy)-phenyl)-oxiran-2-yl methanol 在 4-二甲氨基吡啶 、 六氟异丙醇 、 sodium hydride 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 65.5h， 生成 (2R,3S)-2-(3-benzyloxyphenyl)-5,7-dibenzyloxy-chroman-3-ol
  参考文献：
  名称：

  Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance

  摘要：

  The high-yielding synthesis of enantiomerically pure epicatechin gallate analogues where the A and/or B-ring hydroxylation is reduced or altered has been achieved by optimising routes to the catechin stereochemistry. The B-ring analogues were synthesised by using an electrophilic ring closure onto an enantiomerically enriched epoxide as a key step. The A and B-ring hydroxyl-deleted analogues were synthesised through a Mitsunobu cyclisation. For the B-ring analogues, the anti- (catechin) stereochemistry was converted to the syn- (epicatechin) stereochemistry by a known oxidation/reduction protocol. Absolute stereochemistry was derived from either a Sharpless epoxidation or asymmetric dihydroxylation. (C) 2014 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.052