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(2S,3S)-4-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylbutanamide | 162255-08-5

中文名称
——
中文别名
——
英文名称
(2S,3S)-4-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylbutanamide
英文别名
(2S,3S)-3-hydroxy-N-methoxy-N,2-dimethyl-4-phenylmethoxybutanamide
(2S,3S)-4-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylbutanamide化学式
CAS
162255-08-5
化学式
C14H21NO4
mdl
——
分子量
267.325
InChiKey
DRUADHXIDDOYPS-WCQYABFASA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    388.6±52.0 °C(Predicted)
  • 密度:
    1.129±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    1
  • 重原子数:
    19
  • 可旋转键数:
    7
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.5
  • 拓扑面积:
    59
  • 氢给体数:
    1
  • 氢受体数:
    4

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    (2S,3S)-4-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylbutanamide吡啶咪唑titanium(IV) isopropylate叔丁基过氧化氢copper(l) iodide 、 4 A molecular sieve 、 potassium tert-butylate二异丁基氢化铝 、 (+)-Weinsaeure-diethylester 作用下, 以 四氢呋喃正己烷二氯甲烷N,N-二甲基甲酰胺甲苯 为溶剂, 反应 16.5h, 生成 Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester
    参考文献:
    名称:
    Aplyronine A, a Potent Antitumor Substance of Marine Origin, Aplyronines B and C, and Artificial Analogues:  Total Synthesis and Structure−Cytotoxicity Relationships
    摘要:
    The enantioselective total synthesis of aplyronine A (1), a potent antitumor substance of marine origin, was achieved by a convergent-approach Three segments 4, 5, and 6, corresponding to the C5-C11, C21-C27, and C28-C34 portions of aplyronine A (1), were prepared using:the Evans aldol reaction and the Sharpless epoxidation as key steps. The coupling reaction of 4 with iodide 7 followed by julia olefination with sulfone 8 gave the C5-C20 segment 9, while the julia coupling reaction between segments 5 and 6 provided the C21-C34 segment 10. Julia olefination between segments 9 and 10 and the subsequent four-carbon homologation reaction led to seco acid 83, which was converted into aplyronine A (1) by Yamaguchi lactonization followed by the introduction of two amino acids. The use of the [(3,4-dimethoxybenzyl)oxy]methyl group as a protecting group for the hydroxyl at C29 was crucial for this synthesis. The enantioselective synthesis of two natural congeners, aplyronines B (2) acid C (3), was also carried out using the intermediates for the synthesis of 1, which determined the absolute stereostructures of 2 and 3 unambiguously. To study the structure-cytotoxicity relationships of aplyronines, artificial analogues of 1 were synthesized and their cytotoxicities were evaluated: the trimethylserine moiety, two hydroxyl groups, and the side-chain portion in 1 turned out to be important in the potent cytotoxicity shown by 1. Biological studies with aplyronine A (1) showed that 1 inhibited polymerization of G-actin to F-actin and depolymerized F-actin to G-actin.
    DOI:
    10.1021/jo9606113
  • 作为产物:
    参考文献:
    名称:
    海洋来源的有效抗肿瘤物质Aplyronine A的合成研究:C21–C34段的立体合成
    摘要:
    丙烯醛A(1)的C21–C34片段2是一种有效的海洋来源抗肿瘤物质,是由酰亚胺11以25个步骤(总收率17%)对映选择性合成的。
    DOI:
    10.1016/0040-4039(94)88035-2
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文献信息

  • Total Synthesis of the Polyether Antibiotic Lonomycin A (Emericid)
    作者:David A. Evans、Andrew M. Ratz、Bret E. Huff、George S. Sheppard
    DOI:10.1021/ja00117a014
    日期:1995.3
    The first asymmetric synthesis of the polyether antibiotic lonomycin has been achieved. The skeleton is assembled through the synthesis and union of two subunits comprising the CI-CII and C12-C3o portions of the structure. These fragments were constructed utilizing auxiliary-based asymmetric aldol and acylation reactions to control the absolute stereochemical relationships in the structure. The majority
    首次不对称合成聚醚类抗生素朗霉素已经实现。骨架是通过两个亚基的合成和结合来组装的,这些亚基包括结构的 CI-CII 和 C12-C30 部分。这些片段是利用基于辅助的不对称醛醇和酰化反应构建的,以控制结构中的绝对立体化学关系。分子聚醚部分中的大部分 1 , Z 氧关系是通过一系列环氧化反应建立的,这些环氧化反应通过分子内杂环化转化为环 D、E 和 F。主要亚基通过高度非对映选择性羟醛反应偶联构建 C11 -C12 键。
  • Enantioselective synthesis of δ-/γ-alkoxy-β-hydroxy-α-alkyl-substituted Weinreb amides via DKR–ATH: application to the synthesis of advanced intermediate of (−)-brevisamide
    作者:Gullapalli Kumaraswamy、Akula Narayana Murthy、Vykunthapu Narayanarao、Sahithya Phani Babu Vemulapalli、Jagadeesh Bharatam
    DOI:10.1039/c3ob41088a
    日期:——
    A method of preparing stereodefined δ-/γ-alkoxy-β-hydroxy-α-alkyl-substituted Weinreb amides containing two successive hydroxyl-alkyl stereocenters has been developed. Further, this strategy coupled with organo-catalyzed asymmetric epoxidation culminates in the synthesis of a critical intermediate of (−)-brevisamide and its diastereomers.
    一种制备立体定义的δ-/γ-烷氧基-β-羟基-α-烷基取代的温雷布酰胺的方法已经开发出来。此外,该策略结合了有机催化的不对称环氧化反应,最终合成了(−)-布雷维酰胺及其二叠体的关键中间体。
  • A novel stereoselective route to some uncommon amino acids
    作者:Clay Pearson、Kenneth L Rinehart、Michihiro Sugano
    DOI:10.1016/s0040-4039(98)02383-1
    日期:1999.1
    of ad-erythro-β-methylaspartic acid analog was achieved in six steps from commercially available material. Evans' aldol reactions were utilized followed by Weinreb amide formation and Mitsunobu inversion to achieve the necessary stereochemistry of the amino acid target. The technique was applied to the synthesis of an aspartic acid analog as well as a diaminobutyric acid analog.
    用市售材料通过六个步骤即可高效合成赤型-β-甲基天冬氨酸类似物。利用埃文斯的醛醇缩合反应,随后形成韦氏脲酰胺和光延反转,以实现氨基酸靶标的必要立体化学。该技术被应用于天冬氨酸类似物以及二氨基丁酸类似物的合成。
  • Lasonolide A:  Structural Revision and Total Synthesis
    作者:Ho Young Song、Jung Min Joo、Jung Won Kang、Dae-Shik Kim、Cheol-Kyu Jung、Hyo Shin Kwak、Jin Hyun Park、Eun Lee、Chang Yong Hong、ShinWu Jeong、Kiwan Jeon、Ji Hyun Park
    DOI:10.1021/jo034930n
    日期:2003.10.1
    The proposed structure of lasonolide A was synthesized employing radical cyclization reactions of beta-alkoxyacrylates for preparation of the tetrahydropyranyl units A and B, but the spectroscopic data did not match those of the natural product. Both enantiomers of a revised structure featuring 17E,25Z double bonds were synthesized, and the (-)-isomer was found to be the biologically active enantiomer.
  • Aplyronine A, a Potent Antitumor Substance of Marine Origin, Aplyronines B and C, and Artificial Analogues:  Total Synthesis and Structure−Cytotoxicity Relationships
    作者:Hideo Kigoshi、Kiyotake Suenaga、Tsuyoshi Mutou、Takeshi Ishigaki、Toshiyuki Atsumi、Hiroyuki Ishiwata、Akira Sakakura、Takeshi Ogawa、Makoto Ojika、Kiyoyuki Yamada
    DOI:10.1021/jo9606113
    日期:1996.1.1
    The enantioselective total synthesis of aplyronine A (1), a potent antitumor substance of marine origin, was achieved by a convergent-approach Three segments 4, 5, and 6, corresponding to the C5-C11, C21-C27, and C28-C34 portions of aplyronine A (1), were prepared using:the Evans aldol reaction and the Sharpless epoxidation as key steps. The coupling reaction of 4 with iodide 7 followed by julia olefination with sulfone 8 gave the C5-C20 segment 9, while the julia coupling reaction between segments 5 and 6 provided the C21-C34 segment 10. Julia olefination between segments 9 and 10 and the subsequent four-carbon homologation reaction led to seco acid 83, which was converted into aplyronine A (1) by Yamaguchi lactonization followed by the introduction of two amino acids. The use of the [(3,4-dimethoxybenzyl)oxy]methyl group as a protecting group for the hydroxyl at C29 was crucial for this synthesis. The enantioselective synthesis of two natural congeners, aplyronines B (2) acid C (3), was also carried out using the intermediates for the synthesis of 1, which determined the absolute stereostructures of 2 and 3 unambiguously. To study the structure-cytotoxicity relationships of aplyronines, artificial analogues of 1 were synthesized and their cytotoxicities were evaluated: the trimethylserine moiety, two hydroxyl groups, and the side-chain portion in 1 turned out to be important in the potent cytotoxicity shown by 1. Biological studies with aplyronine A (1) showed that 1 inhibited polymerization of G-actin to F-actin and depolymerized F-actin to G-actin.
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