(2R,3R)-5-p-methoxybenzyloxy-3-methylpentane-1,2-diol | 158817-23-3

• 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: (2R,3R)-5-p-methoxybenzyloxy-3-methylpentane-1,2-diol
• 英文别名: (2R,3R)-5-[(4-methoxyphenyl)methoxy]-3-methylpentane-1,2-diol
• CAS: 158817-23-3
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: XYMAWSJCHLICHA-RISCZKNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-5-p-methoxybenzyloxy-3-methylpentane-1,2-diol 在 二正丁基氧化锡 、 三乙胺 、 对甲苯磺酰氯 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 8.0h， 以82%的产率得到(R)-2-((R)-4-((4-methoxybenzyl)oxy)butan-2-yl)oxirane
  参考文献：
  名称：

  Total synthesis of two γ-butyrolactone containing compounds (Z,11S)-3,4-trans-11-hydroxy-3-methyldodec-cis-6-en-4-olide and (Z)-3,4-trans-11-oxo-3-methyldodec-cis-6-en-4-olide

  摘要：

  The first total synthesis of (2,11S)-3,4-trans-11-hydroxy-3-methyldodec-cis-6-en-4-olide and (2)-3,4-trans-11-oxo-3-methyldodec-cis-6-en-4-olide was accomplished using Jacobsen hydrolytic kinetic resolution, Ohira-Bestmann reaction, regioselective allcyne addition to terminal carbon atom of epoxide, intramolecular TEMPO/BAIB mediated oxidative lactonization and partial hydrogenation as the key steps. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.021
• 作为产物：
  描述：

  3-[(4-甲氧基苄基)氧基]-1-丙醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 草酰氯 、 L-(+)-酒石酸二乙酯 、 4 A molecular sieve 、 二甲基亚砜 、 三乙胺 作用下， 以 苯 为溶剂， 反应 52.17h， 生成 (2R,3R)-5-p-methoxybenzyloxy-3-methylpentane-1,2-diol
  参考文献：
  名称：

  Synthetic studies on ciguatoxin [1]; construction of the spiro acetal part (C46-C55)

  摘要：

  DOI：

  10.1016/s0040-4020(97)10253-8

文献信息

• Construction of the C46-C55 Fragment of Ciguatoxin
  作者：Takahiro Oka、Akio Murai

  DOI：10.1246/cl.1994.1611

  日期：1994.9

  The compound with all the necessary functional groups of the KLM ring system in ciguatoxin, which is one of the most complicated toxic substances of marine origin, was synthesized stereoselectively. The crucial steps involve construction of the ethynyl alcohol, the δ-valerolactone, and the natural acetals.

  具有西加毒素（一种海洋来源的最复杂的有毒物质）KLM环系统所有必需官能团的化合物被立体选择性地合成了。关键步骤包括构建乙炔醇、δ-戊内酯和天然缩醛。
• InCl3-mediated intramolecular Friedel-Crafts-type cyclization and its application to construct the [6-7-5-6] tetracyclic scaffold of liphagal
  作者：Hao Jiang、LuFeng Tian、ZhenTao Li、Qi Liu、ChuangChuang Li、XinSheng Yao、Zhen Yang

  DOI：10.1007/s11426-011-4454-0

  日期：2012.1

  A unified strategy toward the construction of the [5.7.6]tricyclic skeleton of liphagal is reported, featuring InCl3-mediated intramolecular Friedel-Crafts-type cyclization.

  报告采用了一种统一的策略，以 InCl3 为介导的分子内 Friedel-Crafts 型环化为特色，构建了唇柄醛的 [5.7.6] 三环骨架。
• Synthesis of the C1-C9 fragment of the potent antitumor agent dictyostatin
  作者：Luiz C. Dias、Danilo P. Sant'Ana、Ygor W. Vieira、Caroline C. S. Gonçalves、Dimas J. P. Lima

  DOI：10.1590/s0103-50532012000200022

  日期：——

  We describe herein a short and efficient synthesis of the C1-C9 fragment of the potent antitumor agent dictyostatin. Notable features of this approach include a Sharpless asymmetric epoxidation followed by epoxide opening under Myashita's conditions to introduce the stereogenic centers at C6 and C7, and a Horner-Wadsworth-Emmons type reaction under Ando's conditions to construct the Z-double bond of

  我们在本文中描述了有效的抗肿瘤药dictyostatin的C1-C9片段的短而有效的合成。这种方法的显着特征包括：在Myashita条件下进行Sharpless不对称环氧化，然后环氧化物打开，以在C6和C7处引入立体异构中心；在Ando条件下，进行Horner-Wadsworth-Emmons型反应，以构建1的Z-双键3-（Z，E）-二烯体系。
• Synthesis of the common left-half part of pectenotoxins
  作者：Kenshu Fujiwara、Masanori Kobayashi、Fuyuki Yamamoto、Yu-ichi Aki、Mariko Kawamura、Daisuke Awakura、Seiji Amano、Azusa Okano、Akio Murai、Hidetoshi Kawai、Takanori Suzuki

  DOI：10.1016/j.tetlet.2005.05.062

  日期：2005.7

  The common left-half [C31-C33(OCl-C7)-C40] part of pectenotoxins has been synthesized convergently from the C31-C35, C36-C40, and C1-C7 parts. The C31-C35 part, prepared via a new route shorter than our previous route, was coupled with the C36-C40 part through reductive lithiation and addition reactions to give an adduct stereoselectively, which was converted to a cyclic acetal corresponding to the C31-C40 part. The left-half was synthesized by a three-step process including esterification of the C31-C40 part with the C1-C7 part. (c) 2005 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed couplings to nucleophilic heteroarenes: the total synthesis of (−)-frondosin B
  作者：Chambers C. Hughes、Dirk Trauner

  DOI：10.1016/j.tet.2004.07.041

  日期：2004.10

  The total synthesis of (-)-frondosin B, the enantiomer of naturally-occuring (+)-frondosin B, is described, wherein a palladium-catalyzed cyclization is used to establish the tetracyclic ring system of the natural product. (C) 2004 Elsevier Ltd. All rights reserved.