erythro-3-Benzylamino-3-phenyl-propan-1,2-diol | 93027-52-2

• 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: erythro-3-Benzylamino-3-phenyl-propan-1,2-diol
• CAS: 93027-52-2
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: ZQZSYFCEIPDWIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.49
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  erythro-3-Benzylamino-3-phenyl-propan-1,2-diol 、 叔丁基二甲基氯硅烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以2.6 g的产率得到(1S,2R)-1-(benzylamino)-3-(tert-butyldimethylsilyloxy)-1-phenylpropan-2-ol
  参考文献：
  名称：

  A stereoselective synthesis of (+)-L-733,060 from ethyl (R)-(+)-2,3-epoxypropanoate

  摘要：

  An asymmetric synthesis of neurokinin substance P receptor antagonist (+)-L-733,060 starting from enantiomerically pure ethyl (R)-(+)-2,3-epoxypropanoate (ethyl glycidate) is described The synthesis relies on a diastereoselective reductive animation, regioselective intramolecular epoxide opening, and in situ cyclization as the key steps. (c) 2010 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2009.12.010
• 作为产物：
  描述：

  (4S,5R)-3-benzyl-5-(hydroxymethyl)-4-phenyloxazolidin-2-one 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 erythro-3-Benzylamino-3-phenyl-propan-1,2-diol
  参考文献：
  名称：

  A stereoselective synthesis of (+)-L-733,060 from ethyl (R)-(+)-2,3-epoxypropanoate

  摘要：

  An asymmetric synthesis of neurokinin substance P receptor antagonist (+)-L-733,060 starting from enantiomerically pure ethyl (R)-(+)-2,3-epoxypropanoate (ethyl glycidate) is described The synthesis relies on a diastereoselective reductive animation, regioselective intramolecular epoxide opening, and in situ cyclization as the key steps. (c) 2010 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2009.12.010

文献信息

• Reactivity difference between diphosgene and phosgene in reaction with (2,3-anti)-3-amino-1,2-diols
  作者：A. Hamdach、E.M. El Hadrami、S. Gil、R.J. Zaragozá、E. Zaballos-García、J. Sepúlveda-Arques

  DOI：10.1016/j.tet.2006.04.033

  日期：2006.6

  In reactions of (2,3-anti)-3-amino-1,2-diols with diphosgene and phosgene and their conversion into 1,3-oxazolidin-2-ones, some differences in the stereochemistry of the reactions have been found with these two reagents. The reactions with phosgene afforded the expected cis-oxazolidinones, and in the reaction with diphosgene under the same reaction conditions, the trans-oxazolidinones were also obtained

  在（2,3-抗）-3-氨基-1,2-二醇与双光气和光气的反应以及它们转化为1,3-恶唑烷-2-酮的反应中，已发现反应的立体化学存在一些差异。这两种试剂。与光气的反应提供了预期的顺式-恶唑烷酮，并且在相同的反应条件下与双光气的反应中，还获得了反式-恶唑烷酮。
• Indium-mediated facile synthesis of chiral allylic amines
  作者：J.S Yadav、A Bandyopadhyay、B.V.S Reddy

  DOI：10.1016/s0040-4039(01)01258-8

  日期：2001.9

  An efficient procedure for the synthesis of chiral allylic amines from 5-iodomethyl-2-oxazolidinones using indium metal in refluxing methanol is described.

  描述了一种在回流甲醇中使用铟金属从5-碘甲基-2-恶唑烷酮合成手性烯丙基胺的有效方法。
• Enantioselective Synthesis of 2-Phenyl-9-oxabispidines
  作者：Matthias Breuning、Melanie Steiner

  DOI：10.1055/s-2007-966040

  日期：2007.6

  A small selection of enantiomerically pure 2-phenyl-9-oxabispidines was synthesized in a three to five step procedure from commercially available starting materials. Ring opening of (R,R)-3-phenylglycidol with benzylamine, condensation with (S)-epichlorohydrin to the corresponding cis-2,6-bis(hydroxymethyl)-substituted morpholine intermediate, and final cyclization with a primary amine delivered the desired 2-phenyl-9-oxabispidines in good yields. The substituents at the nitrogen atoms were varied by de­benzylation and subsequent alkylation.

  少量对映体纯度较高的 2-苯基-9-氧杂双环[2-phenyl-9-oxabispidines]是通过三到五个步骤从市场上可买到的起始原料合成的。(R,R)-3-苯基缩水甘油与苄胺开环，与(S)-环氧氯丙烷缩合成相应的顺式-2,6-双（羟甲基）-取代吗啉中间体，最后与伯胺环化，以良好的产率合成出所需的 2-苯基-9-氧杂阿非匹啶。氮原子上的取代基通过去苄基化和随后的烷基化发生变化。
• 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.