(R)-tert-butyl 4-((R)-1'-hydroxy-3'-(trimethylsilyl)prop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate | 129786-70-5

• 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: (R)-tert-butyl 4-((R)-1'-hydroxy-3'-(trimethylsilyl)prop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: (4R)-4-((1R)-1-hydroxy-3-trimethylsilanyl-prop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester；tert-butyl (4R)-4-[(1R)-1-hydroxy-3-trimethylsilylprop-2-ynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 129786-70-5
• 化学式: C₁₆H₂₉NO₄Si
• 分子量: 327.496
• InChiKey: JFHIJWYXKLNPBC-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  (R)-tert-butyl 4-((R)-1'-hydroxy-3'-(trimethylsilyl)prop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 136.25h， 生成 (4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((piperidin-1-yl)methyl)oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel PDMP analogues

  摘要：

  A new series of hybrid PDMP analogues, based both on PDMP and styryl analogues of natural ceramide, has been synthesized from D-serine. The synthetic route was developed such that future introduction of different aryl groups is straightforward. Biological evaluation, both in vitro on rat liver Golgi fractions as well as in HEK-293 and COS-7 cells, revealed two lead compounds with comparable inhibitory potency as PDMP, which could be elaborated to more potent inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.048
• 作为产物：
  描述：

  (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 生成 (R)-tert-butyl 4-((R)-1'-hydroxy-3'-(trimethylsilyl)prop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  WAGNER, ROLF;TILLEY, JEFFERSON W., J. ORG. CHEM., 55,(1990) N6, C. 6289-6291

  摘要：

  DOI：

文献信息

• Preparation of a protected (2S,3S)-.beta.-hydroxyaspartic acid suitable for solid-phase peptide synthesis
  作者：Rolf Wagner、Jefferson W. Tilley

  DOI：10.1021/jo00313a015

  日期：1990.12

  (2S,3S)-N-Boc-3-(benzyloxy)aspartic acid beta-benzyl ester (2), a beta-hydroxyaspartic acid derivative suitably protected for incorporation into peptides by solid-phase synthesis, was synthesized from N-Boc-(R)-serine via the intermediate, [4R-(R*,R*)]-4-[hydroxy[2-(trimethylsilyl)ethynyl]methyl]-2,2-dimethyl-3-oxazolidinecarboxylic acid 1,1-dimethylethyl ester (5). Key transformations involved the ruthenium tetraoxide mediated oxidation of the ethynyl moiety to form the beta-carboxylic acid and, after esterification and oxazolidine ring hydrolysis, dichromate oxidation of the resulting primary alcohol to the alpha-carboxylic acid. The method is suitable for the preparation of gram quantities of 2.

  (2S,3S)-N-Boc-3-(苯甲氧基)天冬氨酸β-苄酯(化合物2)是一种适合通过固相合成法引入肽中的β-羟基天冬氨酸衍生物。该化合物由N-Boc-(R)-丝氨酸通过中间体[4R-(R*,R*)]-4-[羟基(2-(三甲基硅基)炔基)甲基]-2,2-二甲基-3-氧杂环戊烷羧酸1,1-二甲基乙基酯(化合物5)合成而来。 关键转换步骤包括：1) 四氧化钌催化的氧化反应，将炔基部分氧化生成β-羧酸；2) 酯化和氧杂环戊烷环水解后，使用重铬酸氧化所得的伯醇生成α-羧酸。 该方法适用于制备克级规模的化合物2。
• Total Synthesis of Darobactin A
  作者：Marko Nesic、David B. Ryffel、Jonathan Maturano、Michael Shevlin、Scott R. Pollack、Donald R. Gauthier、Pablo Trigo-Mouriño、Li-Kang Zhang、Danielle M. Schultz、Jamie M. McCabe Dunn、Louis-Charles Campeau、Niki R. Patel、David A. Petrone、David Sarlah

  DOI：10.1021/jacs.2c05891

  日期：2022.8.10

  The collaborative total synthesis of darobactin A, a recently isolated antibiotic that selectively targets Gram-negative bacteria, has been accomplished in a convergent fashion with a longest linear sequence of 16 steps from d-Garner’s aldehyde and l-serine. Scalable routes toward three non-canonical amino acids were developed to enable the synthesis. The closure of the bismacrocycle was realized through

  darobactin A（一种最近分离的选择性靶向革兰氏阴性菌的抗生素）的协同全合成已经以收敛方式完成，其最长线性序列为 16 步，从d -Garner 醛和l-丝氨酸开始。开发了针对三种非规范氨基酸的可扩展路线以实现合成。双大环的闭合是通过连续的、卤素选择性的拉洛克吲哚合成来实现的，其中正确的环化顺序被证明对于形成所需的天然产物阻转异构体至关重要。
• 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.
• A short route to N-protected furanomycin, 5′-epi-furanomycin and isofuranomycin derivatives
  作者：Ayan Bandyopadhyay、Benoy K. Pal、Shital K. Chattopadhyay

  DOI：10.1016/j.tetasy.2008.07.032

  日期：2008.8

  A short new route to N-protected L-(+)-furanomycin and two of its isomeric derivatives has been developed, which featured the utility of D-serine as a chiral pool material and ring-closing metathesis as a key ring-forming step. (C) 2008 Elsevier Ltd. All rights reserved.
• Stereospecific Substitution of Silylated Bromoallenes with Organocopper Reagents
  作者：Fabiana D'Aniello、Angèle Schoenfelder、André Mann、Maurizio Taddei

  DOI：10.1021/jo961091e

  日期：1996.1.1