methyl (S)-3,4-bis(tert-butyldimethylsilyloxy)butanoate | 238402-01-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (S)-3,4-bis(tert-butyldimethylsilyloxy)butanoate
• 英文别名: (S)-methyl-3,4-tert-butyldimethylsilyloxy butanoate；methyl (3S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]butanoate
• CAS: 238402-01-2
• 化学式: C₁₇H₃₈O₄Si₂
• 分子量: 362.657
• InChiKey: DLEGOIIYFMOLKK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (S)-3,4-bis(tert-butyldimethylsilyloxy)butanoate 在 dirhodium tetraacetate 对甲苯磺酰叠氮 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 [3-(tert-Butyl-dimethyl-silanyloxy)-5-oxo-cyclopent-1-enyl]-phosphonic acid dimethyl ester
  参考文献：
  名称：

  2-Phosphonocyclopenten-2-ones from ε-tert-butyldimethylsilyloxy-α-diazo-β-ketophosphonates via a rhodium(II)-catalysed C–H insertion reaction

  摘要：

  The exposure of certain primary epsilon-tert-butyldimethylsilyloxy-alpha-diazo-beta-ketophosphonates to the action of catalytic rhodium(II) in refluxing toluene leads to a C-H insertion followed by elimination of the silyloxy group to give 2-phosphonocyclopenten-2-ones in fairly good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00761-x
• 作为产物：
  描述：

  L-苹果酸二甲酯 在 咪唑 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (S)-3,4-bis(tert-butyldimethylsilyloxy)butanoate
  参考文献：
  名称：

  Stereoselective Synthesis of (S,E)-2-(trimethylsilyl)ethyl 3-hydroxy-7- (tritylthio)hept-4-enoate

  摘要：

  (S,E)-2-(三甲基硅基)乙基 3-羟基-7-(三苯甲硫基)庚-4-烯酸酯是通过商业可得的L-苹果酸，采用Julia-Kocienski 烯化偶联方法合成的。该方法为(S,E)-3-羟基-7-巯基庚-4-烯酸提供了一种简洁的合成策略。

  DOI：

  10.2174/157017811794557868

文献信息

• Chemo- and stereoselective dirhodium(II)-catalyzed C-H insertion reaction of 5,6-dioxygenated 2-diazo-3-oxohexanoates: Synthesis of an optically active highly functionalized cyclopentane
  作者：Takayuki Yakura、Akiharu Ueki、Tsuyoshi Kitamura、Kenji Tanaka、Masatake Nameki、Masazumi Ikeda

  DOI：10.1016/s0040-4020(99)00369-5

  日期：1999.6

  1]octane-1-carboxylate (5) via oxonium ylide formation/1,2-shift. On the other hand, a similar treatment of methyl (S)-5,6-bis[tert-butyldimethylsilyl(TBDMS)oxy]-2-diazo-3-oxohexanoate (9a) afforded the C-H insertion product 10 which was directly reduced with lithium aluminum hydride to give stereoselectively (1R,2R,3S,5R)-2,3-bis(TBDMSoxy)-5-hydroxycyclopentanemethanol (13) in 52% yield from 9a.

  （S）-α-重氮-2,2-二甲基-β-氧代-1,3-二氧戊环-2-丁酸（4），在回流的二氯甲烷中用四乙酸dir（II）处理后，得到甲基（1 S， 5 S）-2,2-二甲基-7-氧代-3,8-二氧杂双环[3.2.1]辛烷-1-羧酸酯（5）通过形成叶立德/ 1,2-移位。另一方面，对（S）-5,6-双[叔丁基二甲基甲硅烷基（TBDMS）氧基] -2-重氮-3-氧代己酸甲酯（9a）进行类似处理，得到CH插入产物10，该产物被直接还原为氢化铝锂可选择性立体产生（1 R，2R，3 S，5 R）-2,3-双（TBDMSoxy）-5-羟基环戊烷甲醇（13）从9a的产率为52％。
• Largazole Arrests Cell Cycle at G1 Phase and Triggers Proteasomal Degradation of E2F1 in Lung Cancer Cells
  作者：Li-Chuan Wu、Zhe-Sheng Wen、Ya-Tao Qiu、Xiao-Qin Chen、Hao-Bin Chen、Ming-Ming Wei、Zi Liu、Sheng Jiang、Guang-Biao Zhou

  DOI：10.1021/ml400093y

  日期：2013.10.10

  Aberration in cell cycle has been shown to be a common occurrence in lung cancer, and cell cycle inhibitor represents an effective therapeutic strategy. In this study, we test the effects of a natural macrocyclic depsipeptide largazole on lung cancer cells and report that this compound potently inhibits the proliferation and clonogenic activity of lung cancer cells but not normal bronchial epithelial cells. Largazole arrests cell cycle at G1 phase with up-regulation of the expression of cyclin-dependent kinase inhibitor p21. Interestingly, largazole enhances the E2F1-HDAC1 binding affinity and induces a proteasomal degradation of E2F1, leading to suppression of E2F1 function in lung cancer but not normal bronchial epithelial cells. Because E2F1 is overexpressed in lung cancer tumor samples, these data indicate that largazole is an E2F1-targeting cell cycle inhibitor, which bears therapeutic potentials for this malignant neoplasm.
• Diastereoconvergent Synthesis of <i>trans</i>-5-Hydroxy-6-Substituted-2-Piperidinones by Addition–Cyclization–Deprotection Process
  作者：Chang-Mei Si、Wei Huang、Zhen-Ting Du、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1021/ol5020812

  日期：2014.8.15

  A diastereoselective one-pot approach to access trans-5-hydroxy-6-substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by alpha-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.
• Stereoselective Conjugate Addition of Alkyl Groups to ( S )-4-( tert -Butyldimethylsilyloxy)-2-cyclopentenone Derivatives
  作者：Takayuki Yakura、Kenji Tanaka、Tomoko Kitano、Jun'ichi Uenishi、Masazumi Ikeda

  DOI：10.1016/s0040-4020(00)00686-4

  日期：2000.9

  Reaction of (S)-2-benzenesulfonyl-4-(tert-butyldimethylsilyloxy)-2-cyclopentenone (2) and a 2-methoxycarbonyl congener (3) with R2CuLi or RMgBr-CuI stereoselectively gave (2S,3R,4S)-3-alkyl-2-benzenesulfonyl-4-(tert-butyldimethylsilyloxy)cyclopentanone (4) and its (2S,3S,4S)-2-methoxycarbonyl derivative (5) as a major diastereoisomer. On the other hand, reaction with R3Al in toluene exclusively gave the corresponding 3,4-cis-adducts 6 and 7. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 10.1021/01100308a
  作者：Zeng, Xin、Yin, Biaolin、Hu, Zheng、Liao, Chenzhong、Liu, Jinglei、Li, Shang、Li, Zheng、Nicklaus, Marc C.、Zhou, Guangbiao、Jiang, Sheng

  DOI：10.1021/01100308a

  日期：——