(S)-1-benzyloxy-3-(methoxymethoxy)butane

• 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-benzyloxy-3-(methoxymethoxy)butane
• 英文别名: [(3S)-3-(methoxymethoxy)butoxy]methylbenzene
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: BGWVTNUKGUMXPD-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-benzyloxy-3-(methoxymethoxy)butane 在 正丁基锂 、 dimethyl sulfide borane 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 戴斯-马丁氧化剂 、 三乙胺 、 (+)-二异松蒎基氯硼烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 methyl (7R,9S)-9-(methoxymethoxy)-7-phenylmethoxydec-2-ynoate
  参考文献：
  名称：

  The stereoselective total synthesis of (3R,5R)-sonnerlactone and (3R,5S)-sonnerlactone

  摘要：

  The stereoselective synthesis of (3R,5R)-sonnerlactone (1) and (3R,55)-sonnerlactone (2) has been accomplished starting from L-aspartic acid. Our strategy involves asymmetric allylation, Alder-Rickert reaction and Mitsunobu macrolactonization as the key steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.032
• 作为产物：
  描述：

  (2R)-2-(2-benzyloxyethyl)oxirane 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-1-benzyloxy-3-(methoxymethoxy)butane
  参考文献：
  名称：

  The stereoselective total synthesis of (3R,5R)-sonnerlactone and (3R,5S)-sonnerlactone

  摘要：

  The stereoselective synthesis of (3R,5R)-sonnerlactone (1) and (3R,55)-sonnerlactone (2) has been accomplished starting from L-aspartic acid. Our strategy involves asymmetric allylation, Alder-Rickert reaction and Mitsunobu macrolactonization as the key steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.032

文献信息

• Kinetic resolution of poly(ethylene glycol)-supported carbonates by enzymatic hydrolysis
  作者：Masaki Nogawa、Megumi Shimojo、Kazutsugu Matsumoto、Masayuki Okudomi、Yuji Nemoto、Hiromichi Ohta

  DOI：10.1016/j.tet.2006.05.020

  日期：2006.7

  The enzyme-mediated enantioselective hydrolysis of poly(ethylene glycol) (PEG)-supported carbonates is disclosed. The water-soluble carbonates were prepared by immobilization of a racemic secondary alcohol (4-benzyloxy-2-butanol) onto low-molecular weight (av MW 550 and 750) monometboxy PEG through a carbonate linker. For the screening of the hydrolytic enzymes, the substrate was enantioselectively hydrolyzed by commercially available lipase from porcine pancreas (PPL; Type II, Sigma) to afford the optically active compounds. In this system, the separation of the remaining (S)-substrate and the resulting (R)-alcohol was achieved by an extraction process without a laborious column chromatography. The (S)-carbonate was easily hydrolyzed with K2CO3 to afford the corresponding (S)-alcohol. Other MPEG-supported substrates were also hydrolyzed to afford the corresponding optically active alcohols. (c) 2006 Elsevier Ltd. All rights reserved.
• The stereoselective total synthesis of (3R,5R)-sonnerlactone and (3R,5S)-sonnerlactone
  作者：J.S. Yadav、K. Shiva Shankar、A. Srinivas Reddy、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2012.09.032

  日期：2012.11

  The stereoselective synthesis of (3R,5R)-sonnerlactone (1) and (3R,55)-sonnerlactone (2) has been accomplished starting from L-aspartic acid. Our strategy involves asymmetric allylation, Alder-Rickert reaction and Mitsunobu macrolactonization as the key steps. (C) 2012 Elsevier Ltd. All rights reserved.