(4R)-4-((1S)-1-hydroxy-prop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 160592-93-8

• 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: (4R)-4-((1S)-1-hydroxy-prop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (R)-4-((S)-1-hydroxyprop-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate；tert-butyl (4R)-4-[(1S)-1-hydroxyprop-2-ynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 160592-93-8
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: ZQKGOBZDKLCXMB-ZJUUUORDSA-N

物化性质

• 沸点：
  343.0±32.0 °C(predicted)
• 密度：
  1.111±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  (4R)-4-((1S)-1-hydroxy-prop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 甲醇 、 copper(l) iodide 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 碳酸氢钠 、 二异丙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 三乙胺 、 mineral oil 为溶剂， 反应 25.0h， 生成 benzyl ((2R,3S)-1-hydroxy-5-((R)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-3-methoxypentan-2-yl)carbamate
  参考文献：
  名称：

  Synthesis and Bioactivity of a Brasilicardin A Analogue Featuring a Simplified Core

  摘要：

  An analogue 2 of Brasilicardin A, 1 (BraA), a potent immunosuppressive and cytotoxic agent, was synthesized in Which the natural tricyclic skeleton was replaced with a synthetically more accessible substituted tetrahydronaphthalene core. BraA, this analogue (BraL), and cyclosporine A were tested for their ability to inhibit the proliferation of human T cells upon CD3/CD28 activation. Although BraL did not impact T cell activation over the dose range tested, this study shows the inhibitory activity of BraA on human T cells for the first time.

  DOI：

  10.1021/acs.orglett.5b01712
• 作为产物：
  描述：

  (4R)-4-(1-hydroxy-3-trimethylsilanyl-prop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (R)-tert-butyl 4-((R)-1'-hydroxyprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate 、 (4R)-4-((1S)-1-hydroxy-prop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  On the Substrate Specificity of Dehydration by Lacticin 481 Synthetase

  摘要：

  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.

  DOI：

  10.1021/ja067672v

文献信息

• 1,3-diastereocontrol with bromoallenes. Synthesis of enantiomerically pure β-branched α-amino acids
  作者：Fabiana D'Aniello、André Mann、Maurizio Taddei、Camille-Georges Wermuth

  DOI：10.1016/0040-4039(94)80115-0

  日期：1994.10

  Bromoallenes 3a and 3b derived from (D)-Serine undergo SN2′ alkylation with organo copper reagents to give alkynyl amino alcohol derivatives. These compounds can be further transformed into branched enantiometrically enriched α-amino acids as, for example (L)-Isolcucine and (L)-Alloisoleucine.

  衍生自（D）-丝氨酸的溴代烯3a和3b用有机铜试剂进行S N 2'烷基化，得到炔基氨基醇衍生物。这些化合物可以进一步转化为对映体富集的支链α-氨基酸，例如（L）-异亮氨酸和（L）-异苏氨酸。
• Total synthesis of pyrrolidine alkaloid, Radicamine-B via Stille coupling
  作者：P. Mallesham、B.V.D. Vijaykumar、Dong-Soo Shin、S. Chandrasekhar

  DOI：10.1016/j.tetlet.2011.09.034

  日期：2011.11

  Total synthesis of (-) Radicamine-B is achieved in eight steps from (R)-(+)-Garner aldehyde in a stereoflexible manner involving Stille coupling and one-pot domino epoxidation-pyrrolidine formation as key steps. (C) 2011 Elsevier Ltd. All rights reserved.