(R)-4-[(R)-(tert-butyldimethylsilanyloxy)(phenyl)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester | 1345820-55-4

• 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: (R)-4-[(R)-(tert-butyldimethylsilanyloxy)(phenyl)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4R)-4-[(R)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1345820-55-4
• 化学式: C₂₃H₃₉NO₄Si
• 分子量: 421.652
• InChiKey: PWODOAHRSPDYAF-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-4-[(R)-(tert-butyldimethylsilanyloxy)(phenyl)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 在 甲醇 、 草酰氯 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 17.58h， 生成 tert-butyl N-[(1R,2S)-1-[tert-butyl(dimethyl)silyl]oxy-3-oxo-1-phenylpropan-2-yl]carbamate
  参考文献：
  名称：

  Asymmetric synthesis of a dopamine D1 agonist, dihydrexidine from d-serine

  摘要：

  A scalable asymmetric synthesis of trans-2-amino-6,7-dimethoxy-1-phenyltetralin 2 and its N-nosyl derivative 12 have been achieved from Garner aldehyde derived from easily available D-serine using a stereoselective PhMgBr addition, Wittig reaction and TFA-mediated Friedel-Crafts cyclization as the key steps. The synthesis of dihydrexidine is accomplished from the N-nosyl-2-amino-1-phenyltetralin 12. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.014
• 作为产物：
  描述：

  (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 在 4-二甲氨基吡啶 、 copper(l) iodide 、 二甲基硫 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (R)-4-[(R)-(tert-butyldimethylsilanyloxy)(phenyl)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric synthesis of a dopamine D1 agonist, dihydrexidine from d-serine

  摘要：

  A scalable asymmetric synthesis of trans-2-amino-6,7-dimethoxy-1-phenyltetralin 2 and its N-nosyl derivative 12 have been achieved from Garner aldehyde derived from easily available D-serine using a stereoselective PhMgBr addition, Wittig reaction and TFA-mediated Friedel-Crafts cyclization as the key steps. The synthesis of dihydrexidine is accomplished from the N-nosyl-2-amino-1-phenyltetralin 12. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.014

文献信息

• Asymmetric synthesis of a dopamine D1 agonist, dihydrexidine from d-serine
  作者：Rajesh Malhotra、Amit Ghosh、Rajib Ghosh、Sagar Chakrabarti、Swarup Dutta、Tushar K. Dey、Subho Roy、Sourav Basu、Saumen Hajra

  DOI：10.1016/j.tetasy.2011.08.014

  日期：2011.7

  A scalable asymmetric synthesis of trans-2-amino-6,7-dimethoxy-1-phenyltetralin 2 and its N-nosyl derivative 12 have been achieved from Garner aldehyde derived from easily available D-serine using a stereoselective PhMgBr addition, Wittig reaction and TFA-mediated Friedel-Crafts cyclization as the key steps. The synthesis of dihydrexidine is accomplished from the N-nosyl-2-amino-1-phenyltetralin 12. (C) 2011 Elsevier Ltd. All rights reserved.