4-p-methoxybenzyl-2,3-O-isopropylidene-L-threose | 132352-48-8

• 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: 4-p-methoxybenzyl-2,3-O-isopropylidene-L-threose
• 英文别名: (4R,5S)-5-[(4-methoxyphenyl)methoxymethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 132352-48-8
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: ZYEPRNNGUCKKMQ-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-p-methoxybenzyl-2,3-O-isopropylidene-L-threose 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 (E)-3-((4S,5S)-5-((4-ethoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol
  参考文献：
  名称：

  Conformational diagnosis of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate based on the stereochemical outcomes of representative reactions as compared with those of its 4,5-O-isopropylidene derivatives and on a dichroic exciton chirality method

  摘要：

  In order to gain more insight into the conformation of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate (1) experimentally, some appropriate reactions of 1 and its derivative (S,S)-3, which bears isopropylidene protecting groups, have been executed. The stereochemical outcomes of such reactions as the Diels-Alder reaction, osmium tetraoxide-catalyzed hydroxylation, conjugate addition with amines, and cyclopropanation with phosphonium ylides point to a rigid conformation (1A) in which the vicinal TBDMSO groups, the most bulky substituents, are arranged in an anti relationship, and, therefore, the enoate groups are forced to be gauche each other. A dichroic exciton chirality study has also provided clear-cut evidence for this rigid conformation.

  DOI：

  10.1021/jo00075a024
• 作为产物：
  描述：

  (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 4-p-methoxybenzyl-2,3-O-isopropylidene-L-threose
  参考文献：
  名称：

  A stereoselective total synthesis of 7,8-O-isopropylidene iriomoteolide-3a

  摘要：

  以山口酯化、朱莉娅-科西安斯基烯化、有机催化α-氧化和闭环偏合成反应为关键成键步骤，实现了 7,8-O-isopropylidene iriomoteolide-3a 的立体选择性全合成。

  DOI：

  10.1039/c0ob01253j

文献信息

• Novel Sequential Sigmatropic Rearrangements of Allylic Diols: Application to the Total Synthesis of (−)-Kainic Acid
  作者：Katsunori Kitamoto、Mana Sampei、Yasuaki Nakayama、Takaaki Sato、Noritaka Chida

  DOI：10.1021/ol1026602

  日期：2010.12.17

  Sequential sigmatropic rearrangements (Claisen/Claisen and Claisen/Overman) of enantiopure allylic diols are described. The reactions proceeded in complete diastereoselectivity without protecting group manipulations. The sequential Claisen/Overman rearrangement was successfully applied to the total synthesis of (−)-kainic acid.

  描述了对映纯烯丙基二醇的顺序σ重排（Claisen / Claisen和Claisen / Overman）。反应以完全的非对映选择性进行，没有保护基团的操作。连续的克莱森/奥德曼重排成功地应用于（-）-海藻酸的全合成。
• Chirality Transfers through Sequential Sigmatropic Rearrangements of Allylic Vicinal Diols: Development and Application to Total Synthesis of (-)-Kainic Acid
  作者：Katsunori Kitamoto、Yasuaki Nakayama、Mana Sampei、Masato Ichiki、Naoya Furuya、Takaaki Sato、Noritaka Chida

  DOI：10.1002/ejoc.201200523

  日期：2012.8

  sigmatropic rearrangements starting from enantiopure allylic vicinal diols. Starting from the same allylic diol, the sequential Claisen/Claisen rearrangement can install two identical functional groups in a one-pot reaction, whereas, the sequential Claisen/Overman rearrangement can introduce two different functional groups, both occurring without protecting group manipulation. Both sequential reactions proceeded

  详细描述了从对映体纯烯丙基邻二醇开始的两个连续 sigmatropic 重排。从相同的烯丙基二醇开始，连续克莱森 / 克莱森重排可以在一锅反应中安装两个相同的官能团，而连续克莱森 / 奥弗曼重排可以引入两个不同的官能团，两者都发生在没有保护基操作的情况下。两个连续反应都以完全立体选择性进行，这很容易通过关于烯丙二醇的两个因素的明智选择来预测：（1）羟基的立体化学和（2）烯烃的几何结构。为了证明这种顺序重排方法，我们完成了 (-)-红藻氨酸的全合成，
• Synthesis and biological activities of reveromycin A and spirofungin A derivatives
  作者：Takeshi Shimizu、Takeo Usui、Makoto Fujikura、Makoto Kawatani、Tomoharu Satoh、Kiyotaka Machida、Naoki Kanoh、Je-Tae Woo、Hiroyuki Osada、Mikiko Sodeoka

  DOI：10.1016/j.bmcl.2008.05.054

  日期：2008.7

  Various derivatives of reveromycin A, an inhibitor of eukaryotic cell growth, and spirofungin A, focusing on the 5S hydroxyl group and C18 hemisuccinyl group, were synthesized and their inhibitory effects on both the isoleucyl-tRNA synthetase activity and the survival of osteoclasts, and activities on the morphological reversion of src(ts)-NRK cells were examined. It was found that 2,3-dihydroreveromycin

  合成了真核细胞生长抑制剂Reveromycin A和螺菌素A的各种衍生物，它们分别着重于5S羟基和C18半琥珀酰基团，并且它们对异亮氨酰tRNA合成酶的活性以及破骨细胞的存活以及活性的抑制作用对src（ts）-NRK细胞的形态逆转进行了研究。基于活性和稳定性，发现2，3-二氢阿维霉素A是白霉素A的有前途的衍生物。
• Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide
  作者：Joy Chakraborty、Samik Nanda

  DOI：10.1039/c9ob01504c

  日期：——

  synthesis of naturally occurring paecilomycin C is described here for the first time. Asymmetric Brown allylation, E-selective cross metathesis, and a biomimetic carboxylate assisted intramolecular nucleophilic ring opening of an epoxide were employed to access the enantiopure γ-lactone framework of the natural product. Late stage E-selective Julia-Kocienski olefination was then employed to furnish the

  天然青霉素C的聚合全合成在此首次进行了描述。采用不对称布朗烯丙基化，E-选择性交叉复分解和仿生羧酸盐辅助的环氧化物分子内亲核开环来获得天然产物的对映体纯γ-内酯骨架。然后采用后期E选择性Julia-Kocienski烯化反应以有效方式提供天然产物。
• Ni(II)-Catalyzed Regio- and Diastereoselective Allylation of Grignards Reagents to Chiral Allylic Cyclic Carbonates
  作者：Suk Ku Kang、Dong Gyu Cho、Chan Hee Park、Eun Young Namkoong、Joon Seob Shin

  DOI：10.1080/00397919508015850

  日期：1995.6

  Abstract Reaction of chiral allylic cyclic carbonates with Grignards reagent in the presence of NiCl2(dppe) as a catalyst afforded the alkylated (E)-allylic alcohols with high regio- and diastereoselectivity.

  摘要 在 NiCl2(dppe) 催化剂存在下，手性烯丙基环状碳酸酯与格氏试剂反应得到具有高区域选择性和非对映选择性的烷基化 (E)-烯丙醇。