(5R)-2,2,3,3,9,9,10,10-octamethyl-5-(prop-2-en-1-yl)-4,8-dioxa-3,9-disilaundecane | 1313835-58-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (5R)-2,2,3,3,9,9,10,10-octamethyl-5-(prop-2-en-1-yl)-4,8-dioxa-3,9-disilaundecane
• 英文别名: (R)-5-allyl-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilylundecane；(R)-5-allyl-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecane；(R)-4,6-bis-(tert-butyldimethylsilyloxy)-hex-1-ene；tert-butyl-[(3R)-3-[tert-butyl(dimethyl)silyl]oxyhex-5-enoxy]-dimethylsilane
• CAS: 1313835-58-3
• 化学式: C₁₈H₄₀O₂Si₂
• 分子量: 344.685
• InChiKey: ULXUZWLOTALPDX-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R)-2,2,3,3,9,9,10,10-octamethyl-5-(prop-2-en-1-yl)-4,8-dioxa-3,9-disilaundecane 在 sodium periodate 、 四氧化锇 、 2,6-二叔丁基吡啶 、 水 、 四氯化钛 、 N-甲基吗啉氧化物 、 (+)-鹰爪豆碱 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 32.0h， 生成 (R)-4-benzyl-3-((2R,3S,5S)-5,7-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-2-methylheptanoyl)oxazolidin-2-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluations of Aplyronine A–Mycalolide B Hybrid Compound

  摘要：

  A hybrid compound consisting of aplyronine A and mycalolide B was synthesized, and its biological activities were evaluated. The hybrid compound was found to have somewhat more potent actin-depolymerizing activity than aplyronine A. In contrast, the hybrid compound possessed about 1000-fold less cytotoxicity than aplyronine A. These results indicated that there is no direct correlation between actin-depolymerizing activity and cytotoxicity.

  DOI：

  10.1021/ol300182r
• 作为产物：
  描述：

  5-己烯-3-醇,1-[[(1,1-二甲基乙基)二苯基甲硅烷基]氧代]-,(R)- 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (5R)-2,2,3,3,9,9,10,10-octamethyl-5-(prop-2-en-1-yl)-4,8-dioxa-3,9-disilaundecane
  参考文献：
  名称：

  Prins 环化：(–)-Cryptocaryolone 非对映选择性全合成的新策略

  摘要：

  按照最近开发的用于构建反式-2,6-二取代 3,4 的Prins 环化策略，经过 12 个线性步骤实现了 TBDPS 保护的 (-)-cryptocaryolone 的高度非对映选择性全合成，总产率为 7.1% -二氢吡喃。另一种关键中间体，即顺式-1,3-二醇，是通过瓦克氧化然后酮官能团的羟基定向顺式还原来制备的。在本报告中，证明了 Prins 环化在 TBDPS 保护的 (-)-cryptocaryolone 全合成中的多功能性。该方法涉及的关键步骤是用于构建反式-2,6-二取代二氢吡喃的Prins环化、瓦克氧化和羟基引导的顺式还原反应。

  DOI：

  10.1055/a-2152-0671

文献信息

• Substitution dependent stereoselective construction of bicyclic lactones and its application to the total synthesis of pyranopyran, tetraketide and polyrhacitide A
  作者：B. V. Subba Reddy、Dhanraj O. Biradar、Y. Vikram Reddy、J. S. Yadav、Kiran Kumar Singarapu、B. Sridhar

  DOI：10.1039/c6ob01686c

  日期：——

  A novel bicyclization strategy has been developed for the stereoselective synthesis of bicyclic lactones, i.e. 7-aryl or alkyl-2,6-dioxabicyclo[3.3.1]nonan-3-ones through a domino cyclization of (R)-3-hydroxyhex-5-enoic acid with an aldehyde in the presence of 10 mol% trimethylsilyltriflate under mild conditions. The salient features of this methodology are high yields, excellent selectivity, low catalyst

  已经开发了一种新颖的双环化策略，用于通过（R）-3-羟基己基-的多米诺环合立体选择性合成双环内酯，即7-芳基或烷基-2,6-二氧杂双环[3.3.1] nonan-3-ones。在温和的条件下，在10摩尔％的三甲基甲硅烷基三氟甲基磺酸盐存在下，用醛制成的5-烯酸。该方法的显着特征是高收率，出色的选择性，较低的催化剂负载量和更快的反应时间。该方法已成功地应用于吡喃吡喃，四酮化合物和多杀菌素A的全合成。
• Total Synthesis of Leiocarpin C and (+)-Goniodiol via an Olefin Cross-Metathesis Protocol
  作者：Palakodety Radha Krishna、Munagala Alivelu

  DOI：10.1002/hlca.201000365

  日期：2011.6

  A stereoselective total synthesis of leiocarpin C (2) and (+)‐Goniodiol (1) by applying olefin cross‐metathesis and substrate directed dihydroxylation as the key steps is reported (Scheme 3).

  的立体选择性全合成leiocarpin C（2）和（+） - Goniodiol（1）通过施加烯烃交叉复分解和基板定向二羟基作为关键步骤报道（方案3）。
• Synthesis and Biological Evaluation As Microtubule-Active Agents of Several Tetrahydrofuran and Spiroacetal Derivatives
  作者：M. Carda、J. Murga、J. Panos、C. A. Angulo-Pachon、J. Garcia-Pla、S. Diaz-Oltra、J. A. Marco、C. Trigili、M. Redondo-Horcajo、J. F. Diaz、I. Barasoain

  DOI：10.2174/0929867311320090006

  日期：2013.2.1

  The stereoselective preparation of several molecules containing structural fragments of the tetrahydrofuran and spiroacetal type is described. Their degree of cytotoxicity and their interactions with tubulin have been investigated. It has been confirmed that the tetrahydrofuran derivatives are cytotoxic but, in contrast to previous reports, it has been found that the cytoxicity is not due to interactions with the microtubule network. Furthermore, and also in contrast to a previous report on closely related compounds, the spiroacetal derivatives do show interactions with tubulin, even though the precise mechanism and the binding site still remain to be established.

  本文介绍了几种含有四氢呋喃和螺缩醛结构片段的分子的立体选择性制备方法。研究了它们的细胞毒性程度及其与微管蛋白的相互作用。研究证实，四氢呋喃衍生物具有细胞毒性，但与以前的报告不同的是，研究发现这种细胞毒性并不是由于与微管网络的相互作用造成的。此外，与以前关于密切相关化合物的报告不同的是，螺缩醛衍生物确实与微管蛋白发生了相互作用，尽管其确切机制和结合位点仍有待确定。
• Synthesis of a stereoisomer of wortmannilactone C—failure and success
  作者：Aurélia Dittoo、Damien Brandt、Véronique Bellosta、Janine Cossy

  DOI：10.1016/j.tet.2015.05.050

  日期：2015.9

  A diastereomer of wortmannilactone C was synthesized according to a versatile strategy from tert-butyl 3-hydroxypropanoate and ethyl (R)-3-hydroxybutanoate, by using versatile organometallic reagents to control four stereogenic centers out of five. The successful strategy consists of the construction of the C13-C17 triene by using a Liebeskind coupling and the construction of the C2-C7 triene by utilizing a Horner-Wadsworth-Emmons reaction to form the macrocycle. (C) 2015 Elsevier Ltd. All rights reserved.
• Total Synthesis and Tentative Structural Elucidation of Cryptomoscatone E3: Interplay of Experimental and Computational Studies
  作者：Luiz F. T. Novaes、Ariel M. Sarotti、Ronaldo A. Pilli

  DOI：10.1021/acs.joc.5b01956

  日期：2015.12.18

  A successful combination of computational chemistry and total synthesis was explored to tentatively elucidate the absolute configuration of cryptomoscatone E3, a polyketide isolated from the Brazilian tree Cryptocarya mandiocanna. Two independent synthetic approaches are discussed based on asymmetric allylation, ring closing metathesis, and aldol reactions.