(2R,3R)-2,3-bis[[tert-butyldimethylsilyl]oxy]butane-1,4-dioic acid dimethyl ester | 137445-81-9

• 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: (2R,3R)-2,3-bis[[tert-butyldimethylsilyl]oxy]butane-1,4-dioic acid dimethyl ester
• 英文别名: Dimethyl (2R,3R)-2,3-bis{[tert-butyl(dimethyl)silyl]oxy}butanedioate；dimethyl (2R,3R)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]butanedioate
• CAS: 137445-81-9
• 化学式: C₁₈H₃₈O₆Si₂
• 分子量: 406.667
• InChiKey: UXUMTMVSWMDPQE-ZIAGYGMSSA-N

物化性质

• 沸点：
  363.2±42.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2,3-bis[[tert-butyldimethylsilyl]oxy]butane-1,4-dioic acid dimethyl ester 在 potassium tert-butylate 、 三甲基铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 (2R,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-cyclopentanone
  参考文献：
  名称：

  Ohira, Susumu; Nozaki, Hiroshi; Ando, Masaaki, Agricultural and Biological Chemistry, 1991, vol. 55, # 9, p. 2437 - 2438

  摘要：

  DOI：
• 作为产物：
  描述：

  L-(+)-酒石酸二甲酯 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以88%的产率得到(2R,3R)-2,3-bis[[tert-butyldimethylsilyl]oxy]butane-1,4-dioic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of Artificial HMG-CoA Reductase Inhibitors Based on the Olefination Strategy

  摘要：

  研究了合成光学活性6-氧代-3,5-异丙基二氧六酸酯（4）的方法，这些化合物可作为各种人工类3-羟基-3-甲基戊二酸酰辅酶A（HMG-CoA）还原酶抑制剂的关键前体。通过对来自塔贝酒精或l-酒石酸盐的β,δ-二酮酯进行不对称还原，制备了对映异构体(+)-4，随后经过一系列化学转化，最终得到所需的对映异构体(−)-4，并通过相同的不对称还原方法从d-酒石酸盐出发制得。关键中间体(−)-4最终转化为一种高效的HMG-CoA还原酶抑制剂NK-104。

  DOI：

  10.1246/bcsj.68.364

文献信息

• On the direct 2,3-hydroxyl-group differentiation of tartaric acid esters
  作者：James McNulty、Justin Mao

  DOI：10.1016/s0040-4039(02)00662-7

  日期：2002.5

  Direct desymmetrization of tartaric acid esters with TIPS-triflate proceeds in up to 99% yield giving the useful intermediates 2a–b. Selective reduction of the ester groups provides access to fully differentiated threonolactone derivatives while reduction of both esters of 2a followed by periodate mediated diol cleavage allows access to 2-O-TIPS-protected l-glyceraldehyde.

  用TIPS-三氟甲磺酸酯对酒石酸酯进行直接脱对称，收率高达99％，提供了有用的中间体2a – b。酯基团的选择性还原提供了完全分化的苏糖内酯衍生物的途径，而2a的两种酯的还原，然后是高碘酸盐介导的二醇裂解，则使得能够获得2 - O -TIPS保护的1-甘油醛。
• Synthetic (+)-terrein suppresses interleukin-6/soluble interleukin-6 receptor induced-secretion of vascular endothelial growth factor in human gingival fibroblasts
  作者：Hiroki Mandai、Kazuhiro Omori、Daisuke Yamamoto、Toki Tsumura、Kyouta Murota、Satoshi Yamamoto、Koichi Mitsudo、Soichiro Ibaragi、Akira Sasaki、Hiroshi Maeda、Shogo Takashiba、Seiji Suga

  DOI：10.1016/j.bmc.2014.07.047

  日期：2014.10

  Interleukin (IL)-6 is a proinflammatory cytokine that performs a wide variety of biological functions, including important roles in the progression of chronic inflammatory diseases such as periodontal disease. (+)-Terrein, a secondary bioactive fungal metabolite isolated from Aspergillus terreus, has various biological activities; however, its anti-inflammatory effects are still unknown. The purpose of this study was to examine the effect of synthetic (+)-terrein on IL-6 signaling and related protein production in human gingival fibroblasts. To our knowledge, this study is the first to report that synthetic (+)-terrein is not cytotoxic at concentrations less than 20 μM and suppresses IL-6/soluble IL-6 receptor (sIL-6R)-induced phosphorylation of signal transducer and activator of transcription-3, extracellular signal-regulated kinase 1/2, and c-jun N-terminal kinase 1/2-signaling proteins that are downstream of IL-6 signaling. In addition, synthetic (+)-terrein suppresses IL-6/sIL-6R-induced vascular endothelial growth factor (VEGF) secretion in a concentration-dependent manner (p<0.01). These data suggest that synthetic (+)-terrein has potential anti-IL-6 signaling activity and suppresses VEGF-associated inflammatory disease progression.
• Stereoselective reduction of β,δ-diketo esters derived from tartaric acid. A facile route to optically active 6-oxo-3,5-syn-isopropylidenedioxyhexanoate, a versatile synthetic intermediate of artificial HMG Co-A reductase inhibitors.
  作者：Tatsuya Minami、Kyoko Takahashi、Tamejiro Hiyama

  DOI：10.1016/0040-4039(93)85115-d

  日期：1993.1

  Reduction of beta,delta-diketo esters derived from tartaric acid with HAl(i-Bu)2 gave stereoselectively beta-hydroxy-delta-keto esters which were reduced with NaBH4 and Et2BOMe to beta,delta-syn-dihydroxy esters. This strategy was successfully applied to the synthesis of t-butyl (3R,5S)-6-oxo-3,5-isopropylidenedioxyhexanoate starting from D-tartrate.
• Synthesis of Artificial HMG-CoA Reductase Inhibitors Based on the Olefination Strategy
  作者：Tamejiro Hiyama、Tatsuya Minami、Kyoko Takahashi

  DOI：10.1246/bcsj.68.364

  日期：1995.1

  Synthetic methods were studied for optically active 6-oxo-3,5-isopropylidenedioxyhexanoate esters (4), which could be used as a key precursor of various kinds of artificial analogs of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors. An enantiomer (+)-4 was prepared by asymmetric reduction of β,δ-diketo esters derived from the Taber’s alcohol or l-tartrate followed by a series of chemical transformations, and the desired enantiomer (−)-4 was prepared by the same asymmetric reduction starting from d-tartrate. The key intermediate (−)-4 was finally converted into a highly potent HMG-CoA reductase inhibitor, NK-104.

  研究了合成光学活性6-氧代-3,5-异丙基二氧六酸酯（4）的方法，这些化合物可作为各种人工类3-羟基-3-甲基戊二酸酰辅酶A（HMG-CoA）还原酶抑制剂的关键前体。通过对来自塔贝酒精或l-酒石酸盐的β,δ-二酮酯进行不对称还原，制备了对映异构体(+)-4，随后经过一系列化学转化，最终得到所需的对映异构体(−)-4，并通过相同的不对称还原方法从d-酒石酸盐出发制得。关键中间体(−)-4最终转化为一种高效的HMG-CoA还原酶抑制剂NK-104。
• Ohira, Susumu; Nozaki, Hiroshi; Ando, Masaaki, Agricultural and Biological Chemistry, 1991, vol. 55, # 9, p. 2437 - 2438
  作者：Ohira, Susumu、Nozaki, Hiroshi、Ando, Masaaki、Shirane, Fukue、Kondo, Hirokiyo、Nakayama, Mitsuru

  DOI：——

  日期：——