(R)-1-(benzyloxy)-2-methyl-3-[(tetrahydropyranyl)oxy]propan | 88671-02-7

• 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: (R)-1-(benzyloxy)-2-methyl-3-[(tetrahydropyranyl)oxy]propan
• 英文别名: 2-[(2R)-2-methyl-3-phenylmethoxypropoxy]oxane
• CAS: 88671-02-7
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: LSLAFQWBWWKYPE-IURRXHLWSA-N

物化性质

• 沸点：
  369.6±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (R)-1-(benzyloxy)-2-methyl-3-[(tetrahydropyranyl)oxy]propan 在 jones reagent 、 对甲苯磺酸 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 5.0h， 生成 (-)-(R)-3-benzyloxy-2-methylpropionic acid
  参考文献：
  名称：

  Total synthesis and stereochemistry of (+)-phyllanthocindiol

  摘要：

  DOI：

  10.1021/jo00179a018
• 作为产物：
  描述：

  (2S)-2-甲基-3-(四氢-2H-吡喃-2-氧基)丙醛 在 lithium aluminium tetrahydride 、 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-1-(benzyloxy)-2-methyl-3-[(tetrahydropyranyl)oxy]propan
  参考文献：
  名称：

  Stereochemistry of enacyloxins. Part 5: Synthesis of a C9′-C15′ fragment of enacyloxins, a series of antibiotics from Frateuria sp. W-315

  摘要：

  The C9'-C15' fragment of enacyloxins, a series of antibiotics isolated from Frateuria sp. W-315, was synthesized from diethyl D-tartrate.

  DOI：

  10.1515/hc.2011.007

文献信息

• A Mild and Versatile Method for the Tetrahydropyranylation of Alcohols and Their Detetrahydropyranylation
  作者：J. S. Yadav、Dale Srinivas、Gondi Sudershan Reddy

  DOI：10.1080/00397919808006838

  日期：1998.4

  Abstract An efficient and mild method for tetrahydropyranylation of alcohols and their detetrahydropranylation using NH4Cl is described. This protocol provides a useful alternative tetrahydropyranylation of alcohols and their deprotection at different pH. IICT Communication No. 3709

  摘要 描述了一种使用 NH4Cl 进行醇四氢吡喃化及其脱四氢吡喃化的高效、温和的方法。该协议提供了一种有用的替代四氢吡喃醇及其在不同 ph 值下的脱保护。IICT 通讯第 3709 号
• Diastereofacial selection in nitrile oxide cycloaddition reactions. The anti-directing effect of an allylic oxygen and some new results on the ring metalation of isoxazolines. A synthesis of (.+-.)-blastmycinone
  作者：Alan P. Kozikowski、Arun K. Ghosh

  DOI：10.1021/jo00189a024

  日期：1984.7

  the adducts to known γ-lactones. The stereochemistry associated with the metalation/alkylation of 5-alkoxymethyl-substituted isoxazolines has also been probed in order to further expand the use of these heterocycles as aldol equivalents in natural products total synthesis. A synthesis of (±)-blastmycinone (34) is reported which combines the two foregoing aspects of stereocontrol. The levels of regio-

  已经研究了与腈氧化物与带有烯丙基氧取代基的烯烃的反应有关的非对映选择性的程度。当3-丁烯-2-醇（5）或（+）-（S）-异亚丙基-3-丁烯-1,2-二醇（1）的叔丁基二甲基甲硅烷基醚衍生物为1时，已发现合理的非对映选择性水平。用作双极亲虫。这些环加成反应的立体化学过程已通过将加合物转化为已知的γ-内酯的方法得到严格证明。还探索了与5-烷氧基甲基取代的异恶唑啉的金属化/烷基化有关的立体化学，以进一步扩展这些杂环作为天然产物总合成中的羟醛等效物的用途。据报道，（±）-blastcincinone（34）的合成结合了立体声控制的上述两个方面。还讨论了在由异亚丙基-D-甘油醛制得的顺式和反式二取代的烯烃35和39的环加成反应中发现的区域选择性和立体选择性。给出了手性烯烃与手性腈的反应的单个例子。
• Synthesis of brassinolide and its biosynthetic precursors using methyl 3-hydroxy-2-methylpropionate
  作者：V. A. Khripach、V. N. Zhabinskii、K. V. Parkhimovich、O. V. Gulyakevich

  DOI：10.1134/s1068162009020137

  日期：2009.3

  Formal synthesis of plant hormones that belong to the group of 24α-methylbrassinosteroids, including brassinolide and its biosynthetic precursors with one hydroxyl group in their side chain, was performed. Stereochemistry of a methyl group at the C24 atom was provided by the choice of the desired enanthiomer of methyl-3-hydroxy-2-methylpropionate and by the sequence of its conversions into the chiral

  进行了属于 24α-甲基油菜素类固醇组的植物激素的正式合成，包括油菜素内酯及其侧链具有一个羟基的生物合成前体。C24 原子上甲基的立体化学是通过选择所需的甲基-3-羟基-2-甲基丙酸酯对映异构体及其转化为形成 C23-C28 所必需的手性中间体的顺序来提供的。侧链的片段。(22R,23R)-二醇基团是通过中间体 Δ22-类固醇的 Sharpless 不对称二羟基化引入的，这是低分子砜与类固醇 C22-醛的连接、乙酰化和还原脱硫的连续反应的产物中间体 β-乙酰氧基砜。22-乙酰氧基-23的还原，
• The synthesis of the C-9 to C-21 sector of discodermolide: An efficient route to the C13–14 Z-trisubstituted alkene
  作者：Ge Yang、David C. Myles

  DOI：10.1016/s0040-4039(00)77155-3

  日期：1994.4

  The synthesis of the C-9 to C-21 sector of the immunosuppressive marine natural product discodermolide is described. The C-9 to C-15 subunit is synthesized in five steps from aldehyde 5 using the diene aldehyde cyclocondensation reaction. Diastereoselective alkylation of the previously synthesized C-16 to C-21 subunit by a suitably functionalized C-9 to C-15 synthon (3) leads to the C-9 to C-21 sector of discodermolide.
• An alkylative strategy to the C-13 to C-21 sector of discodermolide
  作者：Ge Yang、David C. Myles

  DOI：10.1016/s0040-4039(00)76205-8

  日期：1994.2

  An approach to the C-13 to C-21 sector of the immunosuppressive marine natural product discodermolide (1) is described. The C-15 to C-16 bond is formed by diastereoselective alkylation of a ketone enolate. Either diastereomer of allkylation Can be obtained by selecting the appropriate counter ion. The C-16 to C-21 subunit is prepared in two steps from 11.