(S)-1-{(4R,5S)-5-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-(4-methoxy-benzyloxy)-pent-2-yn-1-ol | 851387-15-0

• 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: (S)-1-{(4R,5S)-5-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-(4-methoxy-benzyloxy)-pent-2-yn-1-ol
• CAS: 851387-15-0
• 化学式: C₂₄H₃₄O₈
• 分子量: 450.529
• InChiKey: RNJDBUVUZIRRBZ-POHUPDAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  95.84
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-1-{(4R,5S)-5-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-(4-methoxy-benzyloxy)-pent-2-yn-1-ol 在 盐酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-α-D-mannofuranoside
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3S,4S,5R)-trans-3,4-dihydroxy-5-(4-fluorophenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)tetrahydrofuran and (2R,3S,4S,5R)-trans-5-ethynyl-2-(4-fluorophenoxymethyl)-3,4-O-isopropylidene tetrahydrofuran from mannose diacetonide

  摘要：

  Stereoselective synthesis of pharmaceutically interesting chiral tetrahydrofurans starting from mannose diacetonide is reported. A 1,4-diol system derived from mannose diacetonide, through a Mitsunobu reaction was stereo specifically cyclized to give chiral tetrahydrofurans. Both the C-1 and C-4 centers Of D-mannose are successfully exploited to install the requisite side chains. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.046
• 作为产物：
  描述：

  2,3,5,6-di-O-isopropylidene-D-mannofuranose 、 1-but-3-ynyloxymethyl-4-methoxy-benzene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以43%的产率得到(S)-1-{(4R,5S)-5-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-(4-methoxy-benzyloxy)-pent-2-yn-1-ol
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3S,4S,5R)-trans-3,4-dihydroxy-5-(4-fluorophenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)tetrahydrofuran and (2R,3S,4S,5R)-trans-5-ethynyl-2-(4-fluorophenoxymethyl)-3,4-O-isopropylidene tetrahydrofuran from mannose diacetonide

  摘要：

  Stereoselective synthesis of pharmaceutically interesting chiral tetrahydrofurans starting from mannose diacetonide is reported. A 1,4-diol system derived from mannose diacetonide, through a Mitsunobu reaction was stereo specifically cyclized to give chiral tetrahydrofurans. Both the C-1 and C-4 centers Of D-mannose are successfully exploited to install the requisite side chains. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.046