[(2R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester | 160349-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester
• 英文别名: [1-(tert-butyldimethylsilanyloxymethyl)-(2R)-2-oxoethyl]carbamic acid benzyl ester；(R)-benzyl 1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-ylcarbamate
• CAS: 160349-52-0
• 化学式: C₁₇H₂₇NO₄Si
• 分子量: 337.491
• InChiKey: YROPBIGCNIQCDD-HNNXBMFYSA-N

物化性质

• 沸点：
  415.9±45.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(2R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester 在 吡啶 、 盐酸 、 甲醇 、 六氟合硅酸 、 NOVOZYM₄₃₅ 、 sodium hydride 、 sodium carbonate 、 臭氧 、 N,N-二异丙基乙胺 、 lithium chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 、 乙酸乙酯 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 79.75h， 生成
  参考文献：
  名称：

  Reduction of Peptide Character of HIV Protease Inhibitors That Exhibit Nanomolar Potency against Multidrug Resistant HIV-1 Strains

  摘要：

  Novel HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere as a transition state-mimic king structure were synthesized by combining substructures of known HIV protease inhibitors. Among them, TYA5 and TYB5 were proven to be not only potent enzyme inhibitors (K-i = 0.12 nM and 0.10 nM, respectively) but also strong anti-HIV agents (IC50 = 9.5 nM and 66 nM, respectively), even against viral strains with multidrug resistance. Furthermore, insertion of an (E)-alkene dipeptide isostere at the P-1-P-2 position of TYB5 led to development of a purely nonpeptidic protease inhibitor, TYB1 (K-i = 0.38 nM, IC50 = 160 nM).

  DOI：

  10.1021/jm020537i
• 作为产物：
  描述：

  (R)-benzyl 4-(ethylthiocarbonyl)-2,2-dimethyloxazolidine-3-carboxylate 在 咪唑 、 盐酸 、 三乙基硅烷 、 palladium 10% on activated carbon 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 生成 [(2R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  脯氨酸催化的醛醇缩合反应的不对称诱导：2,2-二甲基-1,3-二恶烷-5-酮与无环手性α-支化醛的试剂控制加成反应

  摘要：

  如果醛的α-氧基或α-氨基取代基是无环的，则在试剂立体控制下（在匹配和不匹配的情况下），脯氨酸催化的2，2-二甲基-1，3-二恶烷-5-酮与手性醛的羟醛加成反应。对于环状取代基，在不匹配的情况下醛醇缩合的立体化学结果很难预测。

  DOI：

  10.1002/ejoc.201701073

文献信息

• Total synthesis of a piperidine alkaloid, microcosamine A
  作者：Chada Raji Reddy、Bellamkonda Latha、Kamalkishor Warudikar、Kiran Kumar Singarapu

  DOI：10.1039/c5ob02085a

  日期：——

  The first total synthesis of a novel piperidine alkaloid, microcosamine A, is achieved from commercially available d-serine, d-methyl lactate and 1-octyne as starting materials.

  首次成功从商业可获得的D-丝氨酸、D-甲基乳酸酯和1-辛烯作为起始物质，合成了一种新型哌啶生物碱微孔胺A。
• Biomimetic Total Synthesis and Antimicrobial Evaluation of Anachelin H
  作者：Karl Gademann、Yann Bethuel、Hans H. Locher、Christian Hubschwerlen

  DOI：10.1021/jo701402b

  日期：2007.10.1

  biomimetic total synthesis of the iron chelator anachelin H isolated from the cyanobacterium Anabaena cylindrica is reported. A first generation approach delivered one enantiomeric series of the polyketide fragment. Comparison of the 1H NMR data suggested the relative configuration of this anachelin fragment. The relative and absolute configuration of anachelin H was then established by total synthesis. A

  从蓝细菌中分离的铁螯合剂anachelin H的第一仿生全合成鱼腥白茅报道。第一代方法递送了聚酮化合物片段的一个对映体系列。所述的比较1个H NMR数据表明本anachelin片段的相对构型。然后通过全合成确定了阿奇奇林H的相对和绝对构型。第二代方法涉及N，N的酶促转化-二甲基酪胺形成色胺色团。已证明在该反应过程中该产物激活了酪氨酸酶，该色胺色团可以用作酪氨酸酶的活化剂。针对一组11种细菌和真菌病原体对Anachelin H进行了评估，发现针对卡他莫拉菌的中度抗生素活性（32μg/ mL）。
• Total Synthesis of Anachelin H
  作者：Karl Gademann、Yann Bethuel

  DOI：10.1021/ol048068x

  日期：2004.12.1

  [structure: see text] The first total synthesis of anachelin H is reported. Starting from L-Ser, a stereodivergent synthesis of the polyketide fragment resulting in all possible diastereoisomers is described. The alkaloid peptide fragment is prepared via a tellurium-mediated oxidative aza annulation as the key step. Coupling of the fragments gave synthetic anachelin H, which was found to be identical to a sample

  [结构：见正文]报道了安那林H的第一个全合成。从L-Ser开始，描述了导致所有可能的非对映异构体的聚酮化合物片段的立体发散合成。通过碲介导的氧化氮杂环化法制备生物碱肽片段是关键步骤。片段的偶联产生了合成的安那奇林H，其与天然产物的样品相同，因此通过全合成证实了构型。
• C-Functionalized chiral dioxocyclam and cyclam derivatives with 1,2,3-triazole units: synthesis, complexation properties and crystal structures of copper(<scp>ii</scp>) complexes
  作者：A.-S. Felten、N. Petry、B. Henry、N. Pellegrini-Moïse、K. Selmeczi

  DOI：10.1039/c5nj01927c

  日期：——

  the skeleton were designed as valuable bifunctional chelating agents for applications in nuclear medicine. These macrocyclic chelators were prepared via a multi-step sequence involving α- and β-amino acids, and their copper(II) complexation properties were evaluated. A solution structure in which the triazoles are in axially coordinating positions was proposed for the [Cu(anti-27)]2+ complex. Promising

  新Ç -官能化顺式-和反与骨架内连接于碳原子数为1,2,3-三唑单元-dioxocyclam和cyclam衍生物被设计为在核医学应用中有价值的双功能螯合剂。这些大环螯合剂是通过涉及α-和β-氨基酸的多步骤序列制备的，并评估了它们的铜（II）络合特性。针对[Cu（anti - 27）] 2+提出了三唑位于轴向配位位置的溶液结构复杂的。关于络合动力学（<10 s）和酸辅助解离的拟一级半衰期（t 1/2 = 3.21 d，5 M HCl，50°C），已经获得了令人鼓舞的结果。
• Stereoselective allylation reactions of acyclic and chiral α-amino-β-hydroxy aldehydes
  作者：In-Soo Myeong、Yong-Taek Lee、Sang-Hyun Lee、Changyoung Jung、Jin-Seok Kim、Seok-Hwi Park、Jihun Kang、Seung-Jong Lee、In-Hae Ye、Won-Hun Ham

  DOI：10.1016/j.tetasy.2017.07.002

  日期：2017.8

  Stereoselective allylation reactions of acyclic and chiral alpha-amino-beta-hydroxy aldehydes affording chiral beta-amino-alpha,gamma-diols are described. Several Lewis acids (BF3-OEt2, SnCl4, TiCl4, ZnCl2, and MgBr2-OEt2) were employed to mediate the allylation reactions. The reactions of anti-oc-NHCbz-B-OTBS substrates mediated by SnCl4 afforded syn-selective products. The same reaction conditions also gave satisfactory results for the reactions of syn-alpha-NHCbz-beta-OTBS substrates. The mechanism involves alpha-chelation between the amido group and aldehyde oxygen. (C) 2017 Elsevier Ltd. All rights reserved.