1,1-dimethylethyl 4-(S)-2,2-dimethyl-4-(2-propenyl)oxazolidine-3-carboxylate | 860264-38-6

• 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: 1,1-dimethylethyl 4-(S)-2,2-dimethyl-4-(2-propenyl)oxazolidine-3-carboxylate
• 英文别名: tert-butyl (S)-4-allyl-2,2-dimethyloxazolidine-3-carboxylate；(S)-tert-butyl 4-allyl-2,2-dimethyloxazolidine-3-carboxylate；tert-butyl (4S)-2,2-dimethyl-4-prop-2-enyl-1,3-oxazolidine-3-carboxylate
• CAS: 860264-38-6
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: XVMMPDOUUWUBFG-JTQLQIEISA-N

物化性质

• 沸点：
  294.4±33.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl 4-(S)-2,2-dimethyl-4-(2-propenyl)oxazolidine-3-carboxylate 在 咪唑 、 copper(II) choride dihydrate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.5h， 生成 (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-ylcarbamate
  参考文献：
  名称：

  Chemo-enzymatic synthesis of the azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin

  摘要：

  The enzymatic resolution of the N-phenylacetyl derivative of racemic homoserine lactone with penicillin G acylase immobilized on Eupergit C gave (R)-(+)-alpha-amino-gamma-butyrolactone and (S)-(-)-alpha-N-phenylacetamido-gamma-butyrolactone in high enantiomeric purity (ee >99%) and 46-47% yields for each enantiomer. The enantiomers were converted into azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin using Wittig olefination, catalytic ring-closing metathesis (RCM), and stereoselective dihydroxylation with OsO4 in 29% overall yield over 11 high yielding steps. Enzyme inhibition studies showed that 1,4-dideoxyallonojirimycin is a better beta-glucosidase inhibitor (IC50 32.4 mu M toward beta-glucosidase from almonds) and a better beta-galactosidase inhibitor (IC50 5.9 mM for beta-galactosidase from Aspergillus oryzae) than 1,4-dideoxymannojirimycin (IC50 2.86 mM and 12.5 mM for beta-glucosidase and beta-galactosidase, respectively). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.015
• 作为产物：
  描述：

  甲基三苯基溴化膦 、 2,2-二甲基-4-(2-氧代乙基)?唑啉-3-羧酸-(S)-叔丁酯 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 62.0h， 以93%的产率得到1,1-dimethylethyl 4-(S)-2,2-dimethyl-4-(2-propenyl)oxazolidine-3-carboxylate
  参考文献：
  名称：

  C-烯丙基氨基糖与烯基恶唑烷的交叉复分解是合成C-氨基糖基α-氨基酸的关键步骤。1含有C-糖肽的氨基糖的途径

  摘要：

  描述了一般获得的新型糖α-氨基酸，其由亚氨基呋喃糖和亚氨基吡喃糖残基组成，所述亚氨基呋喃糖和亚氨基吡喃糖残基通过烷基链与缩水甘油基连接。通过相同的反应顺序制备了一组八种化合物，其中涉及的第一步是由Grubbs Ru-卡宾催化的各种N -Cbz保护的烯丙基C-亚氨基糖苷与N -Boc-乙烯基-和N的交叉复分解（CM）。-Boc-烯丙基氧唑烷。CM产品（E-和Z-烯烃的混合物）的分离产率在40-70％范围内变化。通过首先使用原位生成的二酰亚胺还原碳-碳双键，然后揭示N，来详细说明每种混合物-Joc试剂氧化恶唑烷环产生的-Boc甘氨酰基[CH（BocNH）CO 2 H]。所有氨基酸均以其甲基酯为特征。通过连续的羧基和氨基与1-苯基丙氨酸衍生物偶联，将模型C-亚氨基糖基-2-氨基戊酸插入三肽中，以证明这些糖氨基酸在设计的糖肽合成中的潜力。

  DOI：

  10.1021/jo050494o

文献信息

• Stereoselective total synthesis of alkaloid caulophyllumine B using iterative olefin cross-metathesis protocol
  作者：Palakodety Radha Krishna、Bonepally Karunakar Reddy

  DOI：10.1016/j.tetlet.2010.09.079

  日期：2010.12

  Herein we report the first total synthesis of alkaloid caulophyllumine B in 14 steps by an iterative olefin cross-metathesis strategy from l-glutamic acid.

  在本文中，我们报道了由I-谷氨酸通过迭代烯烃交叉复分解策略在14个步骤中首次合成生物碱花青素B。
• Unified Approach to the Asymmetric Synthesis of Higher Homologues of (3-Quinolyl)-alanine
  作者：Shital K. Chattopadhyay、Indranil Kundu

  DOI：10.1080/00397911.2014.882002

  日期：2014.7.18

  A new protocol based on a palladium-catalyzed Heck reaction of an amino acid-derived vinyl unit with 3-bromoquinoline has been developed to access the title compounds in good yield and optical purity.
• Chemo-enzymatic synthesis of the azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin
  作者：Mallam Venkataiah、Gowrisankar Reddipalli、Lakshmi Swarnalatha Jasti、Nitin W. Fadnavis

  DOI：10.1016/j.tetasy.2011.10.015

  日期：2011.11

  The enzymatic resolution of the N-phenylacetyl derivative of racemic homoserine lactone with penicillin G acylase immobilized on Eupergit C gave (R)-(+)-alpha-amino-gamma-butyrolactone and (S)-(-)-alpha-N-phenylacetamido-gamma-butyrolactone in high enantiomeric purity (ee >99%) and 46-47% yields for each enantiomer. The enantiomers were converted into azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin using Wittig olefination, catalytic ring-closing metathesis (RCM), and stereoselective dihydroxylation with OsO4 in 29% overall yield over 11 high yielding steps. Enzyme inhibition studies showed that 1,4-dideoxyallonojirimycin is a better beta-glucosidase inhibitor (IC50 32.4 mu M toward beta-glucosidase from almonds) and a better beta-galactosidase inhibitor (IC50 5.9 mM for beta-galactosidase from Aspergillus oryzae) than 1,4-dideoxymannojirimycin (IC50 2.86 mM and 12.5 mM for beta-glucosidase and beta-galactosidase, respectively). (C) 2011 Elsevier Ltd. All rights reserved.
• Cross-Metathesis of <i>C</i>-Allyl Iminosugars with Alkenyl Oxazolidines as a Key Step in the Synthesis of <i>C</i>-Iminoglycosyl α-Amino Acids.¹ A Route to Iminosugar Containing <i>C</i>-Glycopeptides
  作者：Alessandro Dondoni、Pier Paolo Giovannini、Daniela Perrone

  DOI：10.1021/jo050494o

  日期：2005.7.1

  oxazolidine ring by the Jones reagent. All amino acids were characterized as their methyl esters. The insertion of a model C-iminoglycosyl-2-aminopentanoic acid into a tripeptide via sequential carboxylic and amino group coupling with l-phenylalanine derivatives was carried out as a demonstration of the potential of these sugar amino acids in designed glycopeptide synthesis.

  描述了一般获得的新型糖α-氨基酸，其由亚氨基呋喃糖和亚氨基吡喃糖残基组成，所述亚氨基呋喃糖和亚氨基吡喃糖残基通过烷基链与缩水甘油基连接。通过相同的反应顺序制备了一组八种化合物，其中涉及的第一步是由Grubbs Ru-卡宾催化的各种N -Cbz保护的烯丙基C-亚氨基糖苷与N -Boc-乙烯基-和N的交叉复分解（CM）。-Boc-烯丙基氧唑烷。CM产品（E-和Z-烯烃的混合物）的分离产率在40-70％范围内变化。通过首先使用原位生成的二酰亚胺还原碳-碳双键，然后揭示N，来详细说明每种混合物-Joc试剂氧化恶唑烷环产生的-Boc甘氨酰基[CH（BocNH）CO 2 H]。所有氨基酸均以其甲基酯为特征。通过连续的羧基和氨基与1-苯基丙氨酸衍生物偶联，将模型C-亚氨基糖基-2-氨基戊酸插入三肽中，以证明这些糖氨基酸在设计的糖肽合成中的潜力。