tert-butyl (R)-4-((R)-1-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate | 171618-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: tert-butyl (R)-4-((R)-1-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4R)-4-[(1R)-1-hydroxy-2-methylpropyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 171618-18-1
• 化学式: C₁₄H₂₇NO₄
• 分子量: 273.373
• InChiKey: SHGXEOCOQXKSKR-GHMZBOCLSA-N

物化性质

• 熔点：
  84-86 °C
• 沸点：
  350.6±27.0 °C(predicted)
• 密度：
  1.039±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-4-((R)-1-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate 在 4-二甲氨基吡啶 、 boron trifluoride diacetate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 methyl 4-[(2R,3S)-1-[tert-butyl(dimethyl)silyl]oxy-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentan-3-yl]oxybenzoate
  参考文献：
  名称：

  环肽生物碱Sanjoinine G1及其C-11差向异构体的全合成

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(98)00808-4
• 作为产物：
  描述：

  Boc-L-丝氨酸甲酯 在 sodium tetrahydroborate 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 5.0h， 生成 tert-butyl (R)-4-((R)-1-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  对手性恶唑烷醛类的格氏反应

  摘要：

  在Garner型醛中添加Grignard可以观察到中等程度到高水平的不对称诱导。所得仲醇是用于不对称合成的手性结构单元的重要前体，我们已经证明它们可以容易地转化为各自的γ-羟基-β-氨基醇和β-羟基氨基酸。另外，可以从这些前体获得芳氧基醚，它们是许多天然产物的重要组分。

  DOI：

  10.1016/0040-4020(96)00672-2

文献信息

• 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。
• On the Substrate Specificity of Dehydration by Lacticin 481 Synthetase
  作者：Xingang Zhang、Wilfred A. van der Donk

  DOI：10.1021/ja067672v

  日期：2007.2.1

  Dehydroamino acids are valuable building blocks that are a challenge to incorporate synthetically into unprotected peptides. Lantibiotic synthetases possess dehydration activity that converts Ser and Thr residues in their peptide substrates into dehydroalanine and dehydrobutyrine residues, respectively. We show here that lacticin 481 synthetase can convert the Thr analogues (R)-3-EtSer, (R)-3-vinylSer, (R)-3-ethynylSer, (R)-3-[(E)-propenyl]Ser, and (R)-3-propynylSer into the corresponding dehydroamino acids when incorporated into its peptide substrate. This relaxed substrate specificity holds promise for using the enzyme for synthetic purposes and for lantibiotic engineering. On the other hand, (R)-3-PrSer, (R)-3-iPrSer, and allo-Thr are not substrates for the enzyme.
• 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.
• Han, Byung Hoon; Kim, Yong Chul; Park, Man Ki, Heterocycles, 1995, vol. 41, # 9, p. 1909 - 1914
  作者：Han, Byung Hoon、Kim, Yong Chul、Park, Man Ki、Park, Jeong Hill、Go, Hyun Jung、at al.

  DOI：——

  日期：——
• [EN] ANTI-VIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTI-VIRAUX
  申请人：[en]ALIGOS THERAPEUTICS, INC.

  公开号：WO2023283256A1

  公开（公告）日：2023-01-12

  Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating diseases and/or conditions with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.