tert-butyl ((2R,3R)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-4-methylpentan-2-yl)carbamate | 171618-19-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl ((2R,3R)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-4-methylpentan-2-yl)carbamate
• 英文别名: tert-butyl N-[(2R,3R)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-4-methylpentan-2-yl]carbamate
• CAS: 171618-19-2
• 化学式: C₁₇H₃₇NO₄Si
• 分子量: 347.571
• InChiKey: KJFRVELPNRFZRJ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl ((2R,3R)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-4-methylpentan-2-yl)carbamate 在 palladium on activated charcoal 甲酸铵 、 三苯基膦 、 zinc(II) iodide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Han, Byung Hoon; Kim, Yong Chul; Park, Man Ki, Heterocycles, 1995, vol. 41, # 9, p. 1909 - 1914

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-二甲基-(r,s)-4-甲酰基-2,2-二甲基-3-噁唑啉羧酸乙酯 在 4-二甲氨基吡啶 、 TEA 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 tert-butyl ((2R,3R)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-4-methylpentan-2-yl)carbamate
  参考文献：
  名称：

  Han, Byung Hoon; Kim, Yong Chul; Park, Man Ki, Heterocycles, 1995, vol. 41, # 9, p. 1909 - 1914

  摘要：

  DOI：

文献信息

• Total synthesis of the cyclopeptide alkaloid sanjoinine G1 and its C-11 epimer
  作者：Stephen P. East、Feng Shao、Lorenzo Williams、Madeleine M. Joullié

  DOI：10.1016/s0040-4020(98)00808-4

  日期：1998.10

  The naturally occurring cyclopeptide alkaloid sanjoinine G1 and its C-11 epimer were synthesized in 18 steps from D-serine. The key steps in the synthesis were the formation of the alkylaryl ether linkage via an SNAr reaction with 4-fluorobenzonitrile and the macrocyclization to form the 14-membered ring using a modification of the Schmidt protocol involving an activated pentafluorophenyl ester.

  天然存在的环肽生物碱Sanjoinine G1及其C-11差向异构体由D-丝氨酸分18步合成。合成中的关键步骤是通过与4-氟苄腈的S N Ar反应形成烷基芳基醚键，并使用涉及激活的五氟苯基酯的Schmidt协议进行大环化以形成14元环。
• Sulfation of the Human Cytomegalovirus Protein UL22A Enhances Binding to the Chemokine RANTES
  作者：Xiaoyi Wang、Julie Sanchez、Martin J. Stone、Richard J. Payne

  DOI：10.1002/anie.201703059

  日期：2017.7.10

  UL22A is an 83 amino acid chemokine‐binding protein produced by human cytomegalovirus that likely assists the virus in dampening the host antiviral response. We proposed that UL22A is sulfated on two tyrosine residues and tested this hypothesis through the chemical synthesis of a small library of differentially sulfated protein variants. The (sulfo)proteins were efficiently prepared using a novel β‐selenoleucine

  UL22A是人类巨细胞病毒产生的一种83个氨基酸的趋化因子结合蛋白，可能有助于该病毒减弱宿主的抗病毒反应。我们提出将UL22A硫酸化在两个酪氨酸残基上，并通过化学合成一个小的差异硫酸化蛋白质变体的小文库，验证了这一假设。使用新的β-硒代亮氨酸基序可有效制备（磺基）蛋白，以促进一锅连接-脱硒化学反应。事实证明，UL22A的酪氨酸硫酸化对RANTES结合至关重要，与未修饰的蛋白质相比，双硫酸化变体的结合力提高了2.5个数量级。
• Synthesis and Utility of β-Selenophenylalanine and β-Selenoleucine in Diselenide–Selenoester Ligation
  作者：Xiaoyi Wang、Leo Corcilius、Bhavesh Premdjee、Richard J. Payne

  DOI：10.1021/acs.joc.9b02665

  日期：2020.2.7

  The synthesis of suitably protected beta-selenophenylalanine and beta-selenoleucine amino acids was accomplished from Garner's aldehyde as a common starting point. These selenoamino acids were incorporated into model peptides and shown to facilitate rapid diselenide-selenoester ligation (DSL) with peptide selenoesters which, when coupled with in situ deselenization, afforded native peptide products. The utility of one-pot DSL-deselenization chemistry at phenylalanine and leucine was demonstrated through the rapid synthesis of a glycosylated interferon-gamma fragment and the chemokine-binding protein UL22A, respectively.
• Synthesis and biological properties of a new series of 5-substituted-pyrimidine-L-nucleoside analogues
  作者：Nigel B. Westwood、Richard T. Walker

  DOI：10.1016/s0040-4020(98)00821-7

  日期：1998.10

  trans-4-hydroxy-L-proline (5) has been elaborated into a new series of pyrrolidine-L-nucleoside analogues incorporating non-standard 5-substituted-pyrimidine nucleobases, via the azidopyrrolidines 12 and 13. Those analogues employing an acyl protecting group on the primary hydroxyl functionality underwent radical bromination of the ethyl side chain of the pyrimidine ring, to provide E-5-(2-bromovinyl)uracil-pyrrolidine-L-nucleosides 23-26. Of the compounds assessed for potential antiviral activity only 5-ethyluracil-(benzoyloxymethyl)pyrrolidine 20 was found to be a specific inhibitor of vaccinia virus. (C) 1998 Elsevier Science Ltd. All rights reserved.