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2,2-Dimethyl-propionic acid (3R,4R,5R,6R,9S)-5-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-9-methoxy-4,6-dimethyl-3-triethylsilanyloxy-decyl ester | 179945-04-1

中文名称
——
中文别名
——
英文名称
2,2-Dimethyl-propionic acid (3R,4R,5R,6R,9S)-5-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-9-methoxy-4,6-dimethyl-3-triethylsilanyloxy-decyl ester
英文别名
——
2,2-Dimethyl-propionic acid (3R,4R,5R,6R,9S)-5-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-9-methoxy-4,6-dimethyl-3-triethylsilanyloxy-decyl ester化学式
CAS
179945-04-1
化学式
C30H64O6Si2
mdl
——
分子量
577.006
InChiKey
NVFVKUZMMTZZNQ-IURCNINISA-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

计算性质

  • 辛醇/水分配系数(LogP):
    7.81
  • 重原子数:
    38.0
  • 可旋转键数:
    18.0
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.97
  • 拓扑面积:
    74.22
  • 氢给体数:
    1.0
  • 氢受体数:
    6.0

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:
    2,2-Dimethyl-propionic acid (3R,4R,5R,6R,9S)-5-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-9-methoxy-4,6-dimethyl-3-triethylsilanyloxy-decyl ester吡啶disodium hydrogenphosphate 、 sodium amalgam 、 copper(l) iodide正丁基锂甲酸乙酸酐二异丁基氢化铝戴斯-马丁氧化剂氟化氢吡啶溶剂黄146二甲基亚砜lithium diisopropyl amide 作用下, 以 四氢呋喃甲醇乙醚二氯甲烷 为溶剂, 反应 25.3h, 生成 (2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R)-9-(tert-Butyl-dimethyl-silanyloxy)-23-hydroxy-13,19-dimethoxy-8,10,14,17-tetramethyl-7-methylsulfanylmethoxy-tricosa-2,4,14,20-tetraenoic acid ethyl 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:
    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
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文献信息

  • Total Synthesis of Aplyronine A, a Potent Antitumor Substance of Marine Origin
    作者:Hideo Kigoshi、Makoto Ojika、Takeshi Ishigaki、Kiyotake Suenaga、Tsuyoshi Mutou、Akira Sakakura、Takeshi Ogawa、Kiyoyuki Yamada
    DOI:10.1021/ja00095a072
    日期:1994.8
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