methyl (R)-N-methyl-N-methoxy-3-(4-methoxybenzyloxy)-2-methylpropanoate | 449174-20-3

• 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: methyl (R)-N-methyl-N-methoxy-3-(4-methoxybenzyloxy)-2-methylpropanoate
• 英文别名: (R)-N-methoxy-3-(4-methoxy-benzyloxy)-2,N-dimethyl-propionamide；(R)-N-methoxy-3-((4-methoxybenzyl)oxy)-N,2-dimethylpropanamide；(R)-3-(p-methoxybenzyloxy)-N,2-dimethyl-N-methoxypropionamide；(R)-3-(4-methoxybenzyloxy)-N-methoxy-N,2-dimethylpropanamide
• CAS: 449174-20-3
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: BJIORAZDCPYNJC-LLVKDONJSA-N

物化性质

• 沸点：
  350.7±52.0 °C(predicted)
• 密度：
  1.085±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (R)-N-methyl-N-methoxy-3-(4-methoxybenzyloxy)-2-methylpropanoate 在 samarium diiodide 、 氯代二环己基硼烷 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (2R,3R,4S,5S,6R,7S)-7-(benzyloxy-diisopropyl-silanyloxy)-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-acetoxy-nonan-3-ol
  参考文献：
  名称：

  Toward the Combinatorial Synthesis of Polyketide Libraries:  Asymmetric Aldol Reactions with α-Chiral Aldehydes on Solid Support

  摘要：

  [GRAPHIC]The viability of performing stereocontrolled aldol additions with a-chiral aldehydes attached by a silyl linker to a hydroxymethyl polystyrene resin is demonstrated for boron and titanium enolates. Subsequent ketone reduction and manipulation on the solid support leads to elaborate stereopentad sequences, as occur in 6-deoxyerythronolide B and discodermolide.

  DOI：

  10.1021/ol026046+
• 作为产物：
  描述：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 在 4-二甲氨基吡啶 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 camphor-10-sulfonic acid 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 环己烷 、 水 为溶剂， 反应 3.0h， 生成 methyl (R)-N-methyl-N-methoxy-3-(4-methoxybenzyloxy)-2-methylpropanoate
  参考文献：
  名称：

  Nonanolide (Z)-Cytospolides D、E 及其立体异构体的化学酶促不对称全合成

  摘要：

  据报道，天然存在的癸内酯细胞质 D、E 和六种立体异构体的 (Z)-异构体的化学酶不对称全合成。该合成企业的主要亮点涉及适当官能化的酯化合物的闭环复分解 (RCM) 反应，该反应通过所需的酸和醇片段的 Yamaguchi 偶联组装而成。醇片段通过两种替代的化学酶促过程获得，一种是羟腈裂解酶介导的氢氰化，而脂肪酶催化的酯交换是第二种途径中的关键 sep。酸片段是通过前手性 2-甲基-1,3-丙二醇和 Corey-Bakshi-Shibata (CBS) 介导的立体选择性羰基还原的对映选择性酶解对称 (EED) 构建的。

  DOI：

  10.1002/ejoc.201301365

文献信息

• Total Synthesis of the Boron-Containing Ion Carrier Antibiotic Macrodiolide Tartrolon B
  作者：Johann Mulzer、Markus Berger

  DOI：10.1021/jo035391p

  日期：2004.2.1

  The first total synthesis of the boron-containing macrodiolide antibiotic tartrolon B is reported in full detail. Two convergent approaches to the target compound are described, the first of which eventually failed, due to sensitive functionality. In the second, successful route the key step was a stereoselective boron-mediated aldol addition of a bicyclic acetonide protected ketone to a diene-aldehyde

  详细报道了含硼的大乙交酯抗生素tartrolon B的第一个全合成。描述了两种针对目标化合物的融合方法，由于敏感的功能，第一种方法最终失败。在第二条成功的途径中，关键步骤是将双环丙酮化物保护的酮立体选择性地由硼介导的羟醛加成到二烯醛中。在这种情况下，使用Yamaguchi二聚化大内酯化残基可以完成合成而没有重大问题。
• Studies on the Synthesis of Apoptolidin A. 1. Synthesis of the C(1)−C(11) Fragment
  作者：Masaki Handa、Karl A. Scheidt、Martin Bossart、Nan Zheng、William R. Roush

  DOI：10.1021/jo702250z

  日期：2008.2.1

  A synthesis of the C(1)−C(11) fragment of apoptolidin A has been accomplished by a convergent route involving the stereoselective glycosidation of 9 and the Suzuki cross-coupling reaction of bromodienoate 7 and the vinylborane generated via chemoselective hydroboration of diyne 6 with diisopinocampheylborane.

  细胞凋亡素A的C（1）-C（11）片段的合成已通过一条收敛途径完成，该途径涉及9的立体选择性糖苷化和溴代己酸酯7的铃木交叉偶联反应以及通过二炔6的化学选择性加氢硼化生成的乙烯基硼烷与diisopinocampheylborane。
• Synthetic Studies toward the C32–C46 Segment of Hemicalide. Assignment of the Relative Configuration of the C36–C42 Subunit
  作者：Simon Specklin、Guillaume Boissonnat、Camille Lecourt、Geoffroy Sorin、Marie-Isabelle Lannou、Janick Ardisson、François Sautel、Georges Massiot、Christophe Meyer、Janine Cossy

  DOI：10.1021/acs.orglett.5b00955

  日期：2015.5.15

  The synthesis of five diastereomeric model compounds incorporating the C32-C46 segment of the antitumor marine natural product hemicalide has been achieved through a convergent approach relying on the 1,4-addition of an alkenyl boronate to an alpha,beta-unsaturated delta-lactone followed by alpha- hydroxylation of an enolate and a Julia-Kocienski olefination. Comparison of the H-1 and C-13 NMR data of the model compounds with those of hemicalide enabled the assignment of the relative configuration of the C36-C42 subunit.
• Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations
  作者：Casey Medina、Kyle P. Carter、Michael Miller、Timothy B. Clark、Gregory W. O’Neil

  DOI：10.1021/jo401293a

  日期：2013.9.20

  A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.
• Total Synthesis and Structural Elucidation of (−)-Delactonmycin
  作者：Ivan R. Corrêa、Ronaldo A. Pilli

  DOI：10.1002/anie.200351347

  日期：2003.7.7