(2S,4S)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate | 194933-51-2

• 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: (2S,4S)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate
• 英文别名: (2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl-2-methyl；N-Cbz-cis-4-[(tert-butyldimethylsilyl)oxy]-L-proline methyl ester；(1-benzyloxycarbonyl-(4S)-tert-butyldimethylsilyloxy-(2S)-pyrrolidinyl)carboxylic acid methyl ester；1-O-benzyl 2-O-methyl (2S,4S)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate
• CAS: 194933-51-2
• 化学式: C₂₀H₃₁NO₅Si
• 分子量: 393.555
• InChiKey: CKCJCQFKYYPPQP-IRXDYDNUSA-N

物化性质

• 沸点：
  440.7±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate 在 氢气 、 palladium(II) hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 ((2S,4S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidin-2-yl)diphenylmethanol
  参考文献：
  名称：

  三烯胺介导的Diels-Alder反应对八氢喹啉的对映选择性构建

  摘要：

  在衍生自顺式-羟基脯氨酸的仲胺有机催化剂存在下，发现了使用三硝基胺介导的不对称Diels-Alder反应，该反应使用5-硝基-2,3-二氢-4-吡啶酮衍生物作为亲二烯体。该反应通过内选的[4 + 2]环化途径提供旋光的八氢喹啉。随后的立体选择性脱硝，异构化和/或氢化生成十氢喹啉的发散立体异构体，它们是总合成石蒜生物碱的有用合成子。

  DOI：

  10.1021/acs.orglett.9b00932
• 作为产物：
  描述：

  5-aza-5-carbobenzoxy-2-oxa-3-oxo-bicyclo<2.2.1>heptane 在 咪唑 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 (2S,4S)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Developing microcolin A analogs as biological probes

  摘要：

  Three microcolin A and B analogs have been synthesized. Their biological activity profiles were evaluated against several cell lines, revealing the existence of a structural determinant whose role in mediating the antiproliferative effect of the microcolins has heretofore gone unrecognized. While previously described as potent immunosuppressive natural products, we found that these microcolin analogs possessed no selective cytotoxicity when comparing immune cell versus nonimmune cell proliferation. In addition, the amino-terminus of microcolin A has been modified to incorporate a biotinylated polyethylene glycol linker. The biological activity of this biotinylated microcolin A analog was determined. This affinity reagent was shown to retain limited biological activity and thus can serve as a useful probe for elucidating the mechanism of action of microcolin A. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.020

文献信息

• [EN] PHENYL AMINO PYRIMIDINE BICYCLIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS PHÉNYLAMINO-PYRIMIDINE BICYCLIQUES ET LEURS UTILISATIONS
  申请人：YM BIOSCIENCES AUSTRALIA PTY

  公开号：WO2014000032A1

  公开（公告）日：2014-01-03

  The present invention relates to phenyl amino pyrimidine bicyclic compounds formula (I) which are inhibitors of protein kinases including JAK kinases. In particular the compounds are active against JAK1, JAK2, JAK3 and TYK2 kinases. The kinase inhibitors can be used in the treatment of kinase associated diseases such as immunological and inflammatory diseases including organ transplants; hyperproliferative diseases including cancer and myeloproliferative diseases; viral diseases; metabolic diseases; and vascular diseases.

  本发明涉及苯氨基嘧啶双环化合物的化学式(I)，这些化合物是蛋白激酶（包括JAK激酶）的抑制剂。特别是这些化合物对JAK1、JAK2、JAK3和TYK2激酶具有活性。这些激酶抑制剂可用于治疗与激酶相关的疾病，如免疫和炎症性疾病，包括器官移植；高增殖性疾病，包括癌症和骨髓增殖性疾病；病毒性疾病；代谢性疾病；以及血管性疾病。
• [EN] VLA-4 INHIBITOR<br/>[FR] INHIBITEUR DE VLA-4
  申请人：DAIICHI SEIYAKU CO

  公开号：WO2005121135A1

  公开（公告）日：2005-12-22

  A compound which selectively inhibits bonding between a ligand and α4β1 integrin (VLA-4); a process for producing the compound; and a medicine containing the compound. The compound is one represented by, e.g., the formula (I) or a salt thereof. Also provided is a preventive and/or therapeutic agent which contains the compound or salt as a major component and is effective against diseases attributable to cell adhesion, such as, e.g., inflammatory reaction, autoimmune disease, cancer metastasis, bronchial asthma, nasal obstruction, diabetes, arthritis, psoriasis, multiple sclerosis, inflammatory intestinal disease, and rejection reaction in transplantation. (In the formula, Y1 represents arylene, etc.; V1 represents aryl, etc.; and R11 to R14 each represents H, OH, halogeno, etc.)

  一种选择性抑制配体与α4β1整合素（VLA-4）结合的化合物；一种生产该化合物的方法；以及含有该化合物的药物。该化合物可由例如式（I）或其盐所代表。还提供了一种预防和/或治疗剂，其含有该化合物或盐作为主要成分，并对由细胞粘附引起的疾病具有有效性，例如炎症反应、自身免疫疾病、癌症转移、支气管哮喘、鼻塞、糖尿病、关节炎、牛皮癣、多发性硬化、炎症性肠道疾病和移植排斥反应等（在该式中，Y1代表芳基等；V1代表芳基等；R11至R14分别代表H、OH、卤素等）。
• Synthesis of Microcolin B, a Potent New Immunosuppressant Using an Efficient Mixed Imide Formation Reaction
  作者：Merritt B. Andrus、Wenke Li、Robert F. Keyes

  DOI：10.1021/jo970387x

  日期：1997.8.1

  Microcolin B, a potent new immunosuppressant isolated from blue-green alga Lyngbya majuscula off the Venezuelan coast, has been made using a methyl-directed asymmetric hydrogenation reaction with rhodium on alumina catalyst on lactone 4 for the synthesis of the key (R,R)-2,4-dimethyloctanoic acid fragment 1. A new, direct mixed imide formation reaction was also developed for the production of the unusual prolylpyrrolen-2-one 2 portion of microcolin. The pentafluorophenyl ester of CBZ-proline 5 was reacted with the lithium imidate of lactam 6, providing the mixed imide in 80% yield. Coupling of acid 1 with the N-terminus of the tripeptide, followed by coupling with pyrrolylproline 2, gave microcolin B. The new mixed-imide forming reaction was also applied to a formal total synthesis of microcolin A. The pentafluorophenyl ester of TBS-protected cis-hydroxyproline was coupled with lactam 6, and the resultant imide was converted to the key pyrrolylproline made previously far microcolin A.
• JP2015/3908
  申请人：——

  公开号：——

  公开（公告）日：——