(S)-N-tert-butoxycarbonyl-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanamine | 172097-65-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-N-tert-butoxycarbonyl-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanamine
• 英文别名: tert-butyl N-[(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]carbamate
• CAS: 172097-65-3
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: QYLOHMMLBJJYII-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-tert-butoxycarbonyl-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanamine 在 咪唑 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (2S,3S)-1-(tert-butyldimethylsilyloxy)-3-(tert-butoxycarbonylamino)-2-butanol
  参考文献：
  名称：

  Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols

  摘要：

  The stereoselective addition of Grignard reagents to alpha-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00175-4
• 作为产物：
  描述：

  N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 在 palladium dihydroxide 氢气 、 zinc dibromide 作用下， 反应 22.25h， 生成 (S)-N-tert-butoxycarbonyl-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanamine
  参考文献：
  名称：

  Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine

  摘要：

  A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and alpha-hydroxy-beta-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00741-8

文献信息

• Asymmetric Synthesis of ES-285, an Anticancer Agent Isolated from Marine Sources
  作者：Ana C. Allepuz、Ramón Badorrey、María D. Díaz-de-Villegas、José A. Gálvez

  DOI：10.1002/ejoc.200900828

  日期：2009.12

  The asymmetric synthesis of (2S,3R)-2-amino-3-octanedecanol hydrochloride (ES-285·HCl) was achieved in eight steps in ca. 38 % overall yield from the N-benzylimine-derived from (R)-2,3-O-isopropylidene glyceraldehyde, which is easily available on gram scale from the inexpensive precursor D-mannitol. Highly diastereoselective addition of methylmagnesium bromide to the N-benzylimine was the key step

  (2S,3R)-2-amino-3-octanedecanol 盐酸盐 (ES-285·HCl) 的不对称合成在大约 8 个步骤中完成。来自 (R)-2,3-O-异亚丙基甘油醛的 N-苄亚胺的总产率为 38%，它很容易从廉价的前体 D-甘露醇以克规模获得。将甲基溴化镁高度非对映选择性地添加到 N-苄亚胺中是创建具有适当构型的 vic-氨基醇部分的关键步骤。中间体氨基环氧化物的区域选择性开环能够在 C4 处引入长烃链。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Enantioselective synthesis of fully protected anti 3-amino-2-hydroxy butyrates
  作者：Mireia Pastó、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1016/0957-4166(95)00309-d

  日期：1995.9

  An efficient enantioselective synthesis of fully protected anti 3-amino-2hydroxybutyrates has been developed. Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-butanediol, after a change in the nitrogen protecting group, the primary alcohol was protected by regioselective reduction of the corresponding p-methoxybenzylidene acetal. Formation of the oxazolidine and deprotection of the primary alcohol followed by oxidation afforded protected alpha-hydroxy-beta-amino acids in good yield. Since the source of asymmetry is a catalytic Sharpless epoxidation, both enantiomeric series are available and the methodology developed here is expected to be of broad applicability.
• Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine
  作者：Pedro Merino、Elena Castillo、Santiago Franco、Francisco L. Merchán、Tomas Tejero

  DOI：10.1016/s0040-4020(98)00741-8

  日期：1998.10

  A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and alpha-hydroxy-beta-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols
  作者：Pedro Merino、Elena Castillo、Francisco L Merchan、Tomas Tejero

  DOI：10.1016/s0957-4166(97)00175-4

  日期：1997.6

  The stereoselective addition of Grignard reagents to alpha-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols. (C) 1997 Elsevier Science Ltd.