(2S,3R,4R)-3-(benzyloxy)-4-(methoxymethoxy)hept-6-ene-1,2-diol | 1268616-18-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R,4R)-3-(benzyloxy)-4-(methoxymethoxy)hept-6-ene-1,2-diol
• 英文别名: (2S,3R,4R)-4-(methoxymethoxy)-3-phenylmethoxyhept-6-ene-1,2-diol
• CAS: 1268616-18-7
• 化学式: C₁₆H₂₄O₅
• 分子量: 296.364
• InChiKey: XUXWIINFURRTJA-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R)-3-(benzyloxy)-4-(methoxymethoxy)hept-6-ene-1,2-diol 在 Grubbs catalyst first generation 、 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 (3R,4R,5R)-N-benzyl-4-(benzyloxy)-5-((E)-tetradec-2-en-1-yl)tetrahydrofuran-3-amine
  参考文献：
  名称：

  Total synthesis of (−)-ent-pachastrissamine (ent-Jaspine B)

  摘要：

  The total synthesis of the enantiomer of the tetrahydrofuran containing natural product Jaspine B is reported. The key reactions in the synthesis include formation of the tetrahydrofuran unit by an acid mediated Williamson etherification and a subsequent elaboration with an olefin cross metathesis reaction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.010
• 作为产物：
  描述：

  2-O-benzyl-3,4-O-isopropylidene-L-threitol 在 2-iodoxybenzoic acid 、 4-甲基苯磺酸吡啶 、 magnesium bromide ethyl etherate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 21.17h， 生成 (2S,3R,4R)-3-(benzyloxy)-4-(methoxymethoxy)hept-6-ene-1,2-diol
  参考文献：
  名称：

  Stereoselective total synthesis of (+)-synargentolide A

  摘要：

  The stereoselective synthesis of synargentolide A, a polyhydroxy delta-lactone, has been accomplished from tartaric acid. The key steps in the synthesis involve Keck and Brown allylations and ring closing metathesis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.005

文献信息

• Enantiodivergent total synthesis of microcarpalide from l-tartaric acid
  作者：Kavirayani R. Prasad、Kamala Penchalaiah

  DOI：10.1016/j.tet.2011.03.102

  日期：2011.6

  Stereoselective approach for the synthesis of both enantiomers of bio-active decanolactone microcarpalide is described from L-tartaric acid. The synthesis of the key intermediates en route to the natural product is achieved from L-tartaric acid involving the elaboration of gamma-hydroxy amide derived from tartaric acid and ring opening of an epoxide derived from tartaric acid. (C) 2011 Elsevier Ltd. All rights reserved.
• Stereoselective total synthesis of (+)-synargentolide A
  作者：Kavirayani R. Prasad、Kamala Penchalaiah

  DOI：10.1016/j.tetasy.2010.11.005

  日期：2010.12

  The stereoselective synthesis of synargentolide A, a polyhydroxy delta-lactone, has been accomplished from tartaric acid. The key steps in the synthesis involve Keck and Brown allylations and ring closing metathesis. (C) 2010 Elsevier Ltd. All rights reserved.
• Total synthesis of (−)-ent-pachastrissamine (ent-Jaspine B)
  作者：Kavirayani R. Prasad、Kamala Penchalaiah

  DOI：10.1016/j.tetasy.2011.07.010

  日期：2011.7

  The total synthesis of the enantiomer of the tetrahydrofuran containing natural product Jaspine B is reported. The key reactions in the synthesis include formation of the tetrahydrofuran unit by an acid mediated Williamson etherification and a subsequent elaboration with an olefin cross metathesis reaction. (C) 2011 Elsevier Ltd. All rights reserved.