(R)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazine-2-carboxylic acid ethyl ester | 655249-57-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazine-2-carboxylic acid ethyl ester
• 英文别名: ethyl (5R)-3,6-diethoxy-5-propan-2-yl-2,5-dihydropyrazine-2-carboxylate
• CAS: 655249-57-3
• 化学式: C₁₄H₂₄N₂O₄
• 分子量: 284.356
• InChiKey: ZMTZCKCEAFOBFZ-NFJWQWPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-(R)-11-(2-Hexyl-[1,3]dioxolan-2-yl)-2-methoxymethoxy-undec-4-enal 、 (R)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazine-2-carboxylic acid ethyl ester 在 三乙胺 、 magnesium bromide 作用下， 以 乙腈 为溶剂， 生成 (2S,5R)-3,6-Diethoxy-2-[(E)-(1R,2R)-11-(2-hexyl-[1,3]dioxolan-2-yl)-1-hydroxy-2-methoxymethoxy-undec-4-enyl]-5-isopropyl-2,5-dihydro-pyrazine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  ISP-1（myriocin，thermozymocidin）的不对称全合成，这是在sinclairii代谢产物中有效的免疫抑制原理

  摘要：

  通过利用基于Schlosser修饰的Wittig反应的高选择性E-烯烃形成和使用手性杂环衍生物3-乙酰基-（4 S）-异丙基-1的高非对映选择性醛醇缩合反应，可以实现ISP-1的不对称全合成。3-噻唑烷-2-硫酮和[（5 R）-2,5-二氢-5-异丙基-3,6-二乙氧基吡嗪] -2-基羧酸乙酯。

  DOI：

  10.1016/0040-4039(95)00219-3
• 作为产物：
  描述：

  triethyloxonium fluoroborate 、 (R)-5-Isopropyl-3,6-dioxo-piperazine-2-carboxylic acid ethyl ester 以 二氯甲烷 为溶剂， 以77%的产率得到(R)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Lewis acid- and cationic lithium-mediated diastereoselective aldol-type reaction based on a double chiral recognition manner for the asymmetric synthesis of α-substituted serines

  摘要：

  Diastereoselective aldol-type reaction of ethyl (5R or 5S)-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-pyrazinecarboxylate (5) with chiral aldehyde 7 was investigated by using Sn(OSO2CF3)(2)-N-ethylpiperizine, MgBr2-Et(3)N, n-butyllithium, and lithium diisopropylamide. The mediation mode with Sn(II) between (5R or 5S)-5 and 7 proved to be quite different from that with Mg(II). The two aldol products were converted to the corresponding gamma-lactonic alpha-substituted serines (2S)- and (2R)-10.

  DOI：

  10.1016/0040-4039(95)00725-r

文献信息

• [EN] COMPOUNDS AND METHODS OF TREATING INSULIN RESISTANCE AND CARDIOMYOPATHY<br/>[FR] COMPOSÉS ET PROCÉDÉS DE TRAITEMENT DE L'INSULINORÉSISTANCE ET D'UNE MYOCARDIOPATHIE
  申请人：FORBES MEDI TECH RES INC

  公开号：WO2008083280A1

  公开（公告）日：2008-07-10

  [EN] Novel compounds, compositions comprising compounds, and methods for methods for preparing and using compounds are described herein. Methods of treating or ameliorating various conditions, including insulin resistance, pancreatic beta cell apoptosis, obesity, pro-thrombotic conditions, myocardial infarction, hypertension, dyslipidemia, manifestations of Syndrome X, congestive heart failure, inflammatory disease of the cardiovascular system, atherosclerosis, sepsis, type 1 diabetes, liver damage, and cachexia, by administering compounds described herein. Compounds presented herein may be used to modulate serine palmitoyl transferase activity.
  [FR] L'invention concerne de nouveaux composés, des compositions comprenant les composés et des procédés servant à préparer et à utiliser les composés. L'invention concerne des procédés consistant à traiter ou à améliorer différentes affections, dont l'insulinorésistance, l'apoptose des cellules bêta pancréatiques, l'obésité, des affections prothrombotiques, un infarctus du myocarde, l'hypertension, la dyslipidémie, des manifestations du syndrome X, une insuffisance cardiaque congestive, une maladie inflammatoire du système cardiovasculaire, l'athérosclérose, la sepsie, le diabète de type 1, des lésions hépatiques et la cachexie, en administrant les composés de la présente invention. Les composés de la présente invention peuvent être utilisés pour moduler l'activité de la sérine palmitoyl transférase.
• Lewis acid- and cationic lithium-mediated diastereoselective aldol-type reaction based on a double chiral recognition manner for the asymmetric synthesis of α-substituted serines
  作者：Shigeki Sano、Xiao-Kai Liu、Maki Takebayashi、Yoshimaro Kobayashi、Keiko Tabata、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.1016/0040-4039(95)00725-r

  日期：1995.6

  Diastereoselective aldol-type reaction of ethyl (5R or 5S)-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-pyrazinecarboxylate (5) with chiral aldehyde 7 was investigated by using Sn(OSO2CF3)(2)-N-ethylpiperizine, MgBr2-Et(3)N, n-butyllithium, and lithium diisopropylamide. The mediation mode with Sn(II) between (5R or 5S)-5 and 7 proved to be quite different from that with Mg(II). The two aldol products were converted to the corresponding gamma-lactonic alpha-substituted serines (2S)- and (2R)-10.
• Asymmetric total synthesis of ISP-I (myriocin, thermozymocidin), a potent immunosuppressive principle in the isaria sinclairii metabolite
  作者：Shigeki Sano、Yoshimaro Kobayashi、Tatsuya Kondo、Maki Takebayashi、Shigeki Maruyama、Tetsuro Fujita、Yoshimitsu Nagao

  DOI：10.1016/0040-4039(95)00219-3

  日期：1995.3

  Asymmetric total synthesis of ISP-I has been achieved by utilizing highly selective E-olefin formation based on the Schlosser-modified Wittig reaction and highly diastereoselective aldol reactions employing both chiral heterocyclic derivatives, 3-acetyl-(4S)-isopropyl-1,3-thiazolidine-2-thione and ethyl [(5R)-2,5-dihydro-5-isopropyl-3,6-diethoxypyrazin]-2-yl carboxylate.

  通过利用基于Schlosser修饰的Wittig反应的高选择性E-烯烃形成和使用手性杂环衍生物3-乙酰基-（4 S）-异丙基-1的高非对映选择性醛醇缩合反应，可以实现ISP-1的不对称全合成。3-噻唑烷-2-硫酮和[（5 R）-2,5-二氢-5-异丙基-3,6-二乙氧基吡嗪] -2-基羧酸乙酯。