(4S,5R)-3-(tert-butyloxycarbonyl)-2,2-dimethyl-4-(2-methylpropyl)-oxazolidine-5-carboxylic acid | 177556-06-8

• 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: (4S,5R)-3-(tert-butyloxycarbonyl)-2,2-dimethyl-4-(2-methylpropyl)-oxazolidine-5-carboxylic acid
• 英文别名: (4S,5R)-3-(tert-butyloxycarbonyl)-2,2-dimethyl-4-(2-methylpropyl)oxazolidine-5-carboxylic acid；(4S,5R)-N-tert-butoxycarbonyl-2,2-dimethyl-4-isobutyloxazolidine-5-carboxylic acid；N-Boc-norstatine；(4S,5R)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-(2-methylpropyl)-1,3-oxazolidine-5-carboxylic acid
• CAS: 177556-06-8
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: GTXXJDVFIUWUCK-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3-(tert-butyloxycarbonyl)-2,2-dimethyl-4-(2-methylpropyl)-oxazolidine-5-carboxylic acid 在 4-二甲氨基吡啶 、 potassium fluoride 、 叔丁基氯化镁 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 (3R,4S)-1-(tert-butyloxycarbonyl)-3-triethylsilyloxy-4-(2-methylpropyl)azetidin-2-one
  参考文献：
  名称：

  Synthesis of the C-13 Side Chain Precursors of the 9-Dihydrotaxane Analogue ABT-271

  摘要：

  [GRAPHICS]N-Boc-L-Leucinol was converted to two C-13 side chain precursors of the 9-dihydrotaxane analogue ABT-271. The trans-oxazolidine acid 4 and the cis-Boc-lactam 2b were prepared in 44% and 40% overall yield, respectively, and with excellent (>98%) stereochemical purity.

  DOI：

  10.1021/ol006508o
• 作为产物：
  描述：

  (4S,5S)-3-(tert-butyloxycarbonyl)-2,2-dimethyl-5-ethenyl-4-(2-methylpropyl)oxazolidine 在 ruthenium trichloride 、 sodium periodate 、 碳酸氢钠 作用下， 以 四氯化碳 、 乙腈 为溶剂， 以63%的产率得到(4S,5R)-3-(tert-butyloxycarbonyl)-2,2-dimethyl-4-(2-methylpropyl)-oxazolidine-5-carboxylic acid
  参考文献：
  名称：

  Stereoselective synthesis of (−)-N-Boc-statine and (−)-N-Boc-Norstatine

  摘要：

  An efficient synthesis of optically pure N-Boc-statine (9) and N-Boc-norstatine (11) has been developed via a syn selective Grignard reaction of N-Boc-leucinal with allyl- or vinylmagnesium bromide. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01108-8

文献信息

• An Efficient Synthesis of the Taxane-Derived Anticancer Agent ABT-271
  作者：John A. DeMattei、M. Robert Leanna、Wenke Li、Paul J. Nichols、Michael W. Rasmussen、Howard E. Morton

  DOI：10.1021/jo0057203

  日期：2001.5.1

  ABT-271, 1, has been identified as a promising anticancer agent. ABT-271 is a novel taxane possessing a CS-(R)-hydroxyl group as opposed to a CS-ketone which is present in Taxol and Taxotere. To further evaluate ABT-271 as a potential anticancer agent, an efficient synthesis was developed which allows the large scale synthesis of ABT-271. Ketalization of the 7,9-diol of 9-DHAB-III, 2, allows selective removal of th:e CI-acetate with phenyllithium. The resulting C13-hydroxyl group is then acylated using LiHMDS and beta -lactam 22 to give ABT-271 in protected form. The protecting groups were removed first by acidic hydrolysis followed by basic hydrolysis to provide ABT-271. Application of this synthetic sequence provided over 600 g of ABT-271, 1.
• A Versatile Approach to <i>N</i>-Boc-statine and <i>N</i>-Boc-norstatine Based on the Reduction of 1-Trialkylsilyl Acetylenic Ketones. Strong Remote Effect of the C(1) Substituent on the Stereoselectivity
  作者：Carme Alemany、Jordi Bach、Jaume Farràs、Jordi Garcia

  DOI：10.1021/ol991098t

  日期：1999.12.1

  [GRAPHICS]An efficient, unified approach to chiral, protected beta-hydroxy gamma-amino and alpha-hydroxy beta-amino acids derived from Boc-L-leucine has been accomplished on the basis of the oxazaborolidine-controlled, stereoselective reduction of 1-trialkylsilyl acetylenic ketones; stereoselectivity in the reduction step has shown strong dependence upon C(1) substitution.
• 10-DEACETYLBACCATINE III AND 10-DEACETYL 14 BETA-HYDROXYBACCATINE III DERIVATIVES, A PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：INDENA S.p.A.

  公开号：EP0815095B1

  公开（公告）日：2000-05-24
• 10-DEACETYL-14BETA-HYDROXYBACCATINE III DERIVATIVES, A PROCESS FOR THE PREPARATION THEREOF AND FORMULATIONS CONTAINING THEM
  申请人：INDENA S.p.A.

  公开号：EP0862563A1

  公开（公告）日：1998-09-09
• US5750562A
  申请人：——

  公开号：US5750562A

  公开（公告）日：1998-05-12