(S)-3-(methoxymethoxy)-1-butanol | 73252-36-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-(methoxymethoxy)-1-butanol
• 英文别名: (3S)-3-(methoxymethoxy)butan-1-ol
• CAS: 73252-36-5
• 化学式: C₆H₁₄O₃
• 分子量: 134.175
• InChiKey: AGDCYCRHQFDLPD-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (S)-3-(methoxymethoxy)-1-butanol 在 正丁基锂 、 dimethyl sulfide borane 、 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 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 36.0h， 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：

  ethyl (S)-3-(methoxymethoxy)butanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以85%的产率得到(S)-3-(methoxymethoxy)-1-butanol
  参考文献：
  名称：

  Studies directed toward the total synthesis of streptogramin antibiotics. Enantiospecific approach to the nine-membered macrocycle of griseoviridin

  摘要：

  DOI：

  10.1021/ja00522a085

文献信息

• Studies directed toward the total synthesis of streptogramin antibiotics. Enantiospecific approach to the nine-membered macrocycle of griseoviridin
  作者：A. I. Meyers、Richard A. Amos

  DOI：10.1021/ja00522a085

  日期：1980.1
• 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.