5-苄氧基-2-甲基戊烷-1,3-二醇 | 73814-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-苄氧基-2-甲基戊烷-1,3-二醇
• 英文名称: (2R,3S)-2-methyl-5-phenylmethoxypentane-1,3-diol
• CAS: 73814-98-9；73814-99-0；105560-79-0；143005-16-7
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: LMALYWYRCWWHSP-YPMHNXCESA-N

物化性质

• 沸点：
  382.7±32.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-苄氧基-2-甲基戊烷-1,3-二醇 在 palladium on activated charcoal 吡啶 、 咪唑 、 三氟甲磺酸二丁硼 、 氢气 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4R)-4-benzyl-3-[(2R,3S,5S,6R)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-3-hydroxy-2,6-dimethylheptanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and actin-depolymerizing activity of mycalolide analogs

  摘要：

  Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), was stereoselectively synthesized and was found to have strong actin-depolymerizing activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.078
• 作为产物：
  描述：

  5-benzyloxy-2-pentyn-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 L-(+)-酒石酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 34.5h， 生成 5-苄氧基-2-甲基戊烷-1,3-二醇
  参考文献：
  名称：

  Enantio- and stereocontrolled formation of the bisspiroacetal core of spirolide B

  摘要：

  The bisspiroacetal core of spirolide B, a marine natural toxin, was synthesized from triketone 10 via one-step bisspiroacetalization, methylation, and silylation accompanied by isomerization of the C-15 spirocenter. The equilibrium of two isomers under acidic conditions was also examined. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.156

文献信息

• Synthesis of the polyol chain of (-)-roxaticin.
  作者：Scott D. Rychnovsky、Cesar Rodriguez

  DOI：10.1021/jo00044a007

  日期：1992.8

  Tetraacetonide 19, which incorporates the 10 stereogenic centers of (-)-roxaticin, was chosen as a test case to develop a convergent synthesis of alternating polyol chains. This synthesis uses a stepwise alkylation of dibromide 16 followed by a stereoselective reductive decyanation in a three-fold convergent strategy.
• Total Synthesis of Basiliskamides A and B
  作者：Darren J. Lipomi、Neil F. Langille、James S. Panek

  DOI：10.1021/ol048574m

  日期：2004.9.1

  The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).
• Synthesis and actin-depolymerizing activity of mycalolide analogs
  作者：Kiyotake Suenaga、Saori Miya、Takeshi Kuroda、Tomohisa Handa、Kengo Kanematsu、Akira Sakakura、Hideo Kigoshi

  DOI：10.1016/j.tetlet.2004.05.078

  日期：2004.7

  Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), was stereoselectively synthesized and was found to have strong actin-depolymerizing activity. (C) 2004 Elsevier Ltd. All rights reserved.
• Total Synthesis of Azumamides A and E
  作者：Irene Izzo、Nakia Maulucci、Giuseppe Bifulco、Francesco De Riccardis

  DOI：10.1002/anie.200602033

  日期：2006.11.20
• Stereoselective synthesis of the common polyketide fragment of hoiamides
  作者：M. Seenaiah、S. Chandrasekhar

  DOI：10.1016/j.tetlet.2012.05.103

  日期：2012.8

  Stereoselective synthesis of the polyketide fragment commonly present in hoiamide A, B, and C is described using iterative Crimmins aldol reaction as the key reaction. (C) 2012 Elsevier Ltd. All rights reserved.