(2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxydecanoate | 157824-01-6

• 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: (2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxydecanoate
• 英文别名: (2R,3R,αR)-tert-butyl 2-hydroxy-3-(N-benzyl-N-α-methylbenzylamino)decanoate；tert-butyl (2R,3R)-3-[benzyl-[(1R)-1-phenylethyl]amino]-2-hydroxydecanoate
• CAS: 157824-01-6
• 化学式: C₂₉H₄₃NO₃
• 分子量: 453.665
• InChiKey: OJZJVKYTCMGNFS-XSBVVTFOSA-N

物化性质

• 沸点：
  545.9±45.0 °C(predicted)
• 密度：
  1.030±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxydecanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以92%的产率得到(2R,3R,αR)-2-hydroxy-3-(N-benzyl-N-α-methylbenzyl)aminodecanol
  参考文献：
  名称：

  Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

  摘要：

  An efficient protocol for the transformation of homochiral alpha-hydroxy-beta-amino esters to their alpha-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha,beta-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino-1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-alpha-methylbenzyl protected alpha-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the alpha-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides alpha-amino acids in 94-98% e.e. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00406-8
• 作为产物：
  描述：

  (R)-(+)-N-苄基-1-苯乙胺 、 trans-2-decenoic acid tert-butyl ester 在 正丁基锂 、 (1R)-(-)-(10-camphorsulfonyl)oxaziridine 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以71%的产率得到(2R,3R,αR)-tert-butyl 3-(N-benzyl-N-α-methylbenzyl)amino-2-hydroxydecanoate
  参考文献：
  名称：

  Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

  摘要：

  An efficient protocol for the transformation of homochiral alpha-hydroxy-beta-amino esters to their alpha-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha,beta-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino-1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-alpha-methylbenzyl protected alpha-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the alpha-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides alpha-amino acids in 94-98% e.e. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00406-8

文献信息

• Asymmetric synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid: The unknown amino acid component of microginin
  作者：Mark E. Bannage、Anthony J. Burke、Stephen G. Davies、Christopher J. Goodwin

  DOI：10.1016/s0957-4166(00)86173-x

  日期：1994.1

  Comparison of the 1H and 13C nmr spectroscopic data of the synthetic amino acids with that reported for the naturally occurring material indicates that the relative stereochemisuy of the AHDA found in microginin is syn. The absolute stereochemistry of the natural amino acid is shown to be (2S,3R) by comparison of its reported CD spectrum with that recorded for the synthetic material prepared herein.

  3-氨基-2-羟基癸酸（AHDA）是一种不寻常的氨基酸，据说发生在最近分离的血管紧张素转化酶抑制剂microgipin中。为了阐明天然存在的物质的立体化学，从而完成微紫精的结构分配，AHDA的（2 R，3 R）-反-非对映异构体和（2 S，3 R）顺-非对映异构体均已被采用。准备好了。合成氨基酸的1 H和13 C nmr光谱数据与天然物质报道的数据比较表明，在微ginin中发现的AHDA的相对立体化学为SYN。通过比较其报告的CD光谱与本文制备的合成材料所记录的CD光谱，天然氨基酸的绝对立体化学显示为（2 S，3 R）。
• Asymmetric synthesis of the N-terminal component of microginin: (2S,3R)-3-amino-2-hydroxydecanoic acid, its (2R,3R)-epimer and (3R)-3-aminodecanoic acid
  作者：Mark E Bunnage、Anthony J Burke、Stephen G Davies、Christopher J Goodwin

  DOI：10.1016/0957-4166(94)00372-i

  日期：1995.1

  3-Amino-2-hydroxydecanoic acid (AHDA) is a novel amino acid which has been suggested as the N-terminal component of the recently isolated angiotensin-converting enzyme inhibitor microginin. The naturally occurring amino acid was found to possess syn relative stereochemistry and (2S,3R) absolute stereochemistry when the reported H-1 and C-13 nmr spectroscopic data and the CD data were compared to the spectroscopic data for synthetic (2R,3R)- and (2S,3R)-AHDA. These studies complete the stereochemical assignment of microginin.
• Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide
  作者：Stephen G. Davies、Simon W. Epstein、A.Christopher Garner、Osamu Ichihara、Andrew D. Smith

  DOI：10.1016/s0957-4166(02)00406-8

  日期：2002.8

  An efficient protocol for the transformation of homochiral alpha-hydroxy-beta-amino esters to their alpha-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha,beta-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino-1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-alpha-methylbenzyl protected alpha-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the alpha-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides alpha-amino acids in 94-98% e.e. (C) 2002 Elsevier Science Ltd. All rights reserved.