(4R,5R)-4,5-bis(benzyloxy)hept-6-en-1-ol | 553665-24-0

• 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: (4R,5R)-4,5-bis(benzyloxy)hept-6-en-1-ol
• 英文别名: (4R,5R)-4,5-bis(phenylmethoxy)hept-6-en-1-ol
• CAS: 553665-24-0
• 化学式: C₂₁H₂₆O₃
• 分子量: 326.436
• InChiKey: GLLFLICDGQYWJF-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4,5-bis(benzyloxy)hept-6-en-1-ol 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 48.5h， 生成 (2S,4E,6R,7R)-2-[(1S)-1-(2-methoxyethoxymethoxy)heptyl]-6,7-bis(phenylmethoxy)-2,3,6,7,8,9-hexahydrooxecin-10-one
  参考文献：
  名称：

  Total synthesis of microcarpalide

  摘要：

  A total synthesis of the natural product microcarpalide is described. Ring-closing metathesis of a dienic ester was used as the key step. Mannose was used as the chiral pool material for the construction of the olefinic-acid and a Sharpless asymmetric dihydroxylation reaction provided the chiral precursor for the synthesis of the olefinic-alcohol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00441-6
• 作为产物：
  描述：

  benzyl (E)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside 在 palladium on activated charcoal 吡啶 、 咪唑 、 四丁基氟化铵 、 氢气 、 碘 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 、 锌 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 苯 为溶剂， -78.0~80.0 ℃ 、600.0 kPa 条件下， 反应 25.5h， 生成 (4R,5R)-4,5-bis(benzyloxy)hept-6-en-1-ol
  参考文献：
  名称：

  Total synthesis of microcarpalide

  摘要：

  A total synthesis of the natural product microcarpalide is described. Ring-closing metathesis of a dienic ester was used as the key step. Mannose was used as the chiral pool material for the construction of the olefinic-acid and a Sharpless asymmetric dihydroxylation reaction provided the chiral precursor for the synthesis of the olefinic-alcohol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00441-6

文献信息

• Stereoselective synthesis of (−)-microcarpalide
  作者：Kavirayani R. Prasad、Kamala Penchalaiah、Amit Choudhary、Pazhamalai Anbarasan

  DOI：10.1016/j.tetlet.2006.11.027

  日期：2007.1

  A stereoselective approach for the synthesis of the bio-active decanolactone (-)-microcarpalide was achieved from chiral pool tartaric acid. The synthesis of pivotal intermediates en route to the decanolactone was achieved from a-benzyloxy aldehydes derived from L- and D-tartaric acid. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.
• Total synthesis of microcarpalide
  作者：Mukund K. Gurjar、Ravi Nagaprasad、C.V. Ramana

  DOI：10.1016/s0040-4039(03)00441-6

  日期：2003.3

  A total synthesis of the natural product microcarpalide is described. Ring-closing metathesis of a dienic ester was used as the key step. Mannose was used as the chiral pool material for the construction of the olefinic-acid and a Sharpless asymmetric dihydroxylation reaction provided the chiral precursor for the synthesis of the olefinic-alcohol. (C) 2003 Elsevier Science Ltd. All rights reserved.