benzyl N-[(2S)-1-[[(2S)-1-hydroxy-3-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate | 142981-11-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl N-[(2S)-1-[[(2S)-1-hydroxy-3-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 142981-11-1
• 化学式: C₁₆H₂₂N₂O₅
• 分子量: 322.361
• InChiKey: KVLIXTSZINGKAO-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S)-1-[[(2S)-1-hydroxy-3-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate 在 tin 、 二甲基硫 、 臭氧 作用下， 以 乙醇 为溶剂， 反应 6.5h， 生成 [(S)-1-((3S,4S)-4,6-Dihydroxy-5,5-dimethyl-tetrahydro-pyran-3-ylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Barbier-type allylation of chiral α-aminoaldehydes: Dependence of the stereochemical outcome on metal and allylic halide

  摘要：

  The chiral beta-hydroxy-alpha-aminoaldehydes of type 1 react smoothly with allyl-, 3,3-dimethylallyl bromide and 2-bromo-cyclohexene in the presence of tin or zinc dust to give the homoallylic alcohols of type 3. For the first time it is shown that the diastereoselectivity in in the Barbier reaction can be influenced by the choice of metal and/or allylic halide. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00050-1
• 作为产物：
  描述：

  [(S)-2-Methyl-1-((3R,4R,5S,6R)-2,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl)-propyl]-carbamic acid benzyl ester 在 sodium tetrahydroborate 、 sodium periodate 作用下， 生成 benzyl N-[(2S)-1-[[(2S)-1-hydroxy-3-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Kolter, Thomas; Klein, Annegret; Giannis, Athanassios, Angewandte Chemie, 1992, vol. 104, # 10, p. 1394 - 1395

  摘要：

  DOI：

文献信息

• Z-Selective olefination of base-sensitive chiral β-hydroxy-α-aminoaldehydes using a modified Horner-Wadsworth-Emmons reaction
  作者：Frank Rübsam、Antje M. Evers、Christoph Michel、Athanassios Giannis

  DOI：10.1016/s0040-4020(96)01091-5

  日期：1997.2

  The HWE reaction of base-sensitive chiral beta-hydroxy-alpha-aminoaldehydes (serinals) was achieved under mild conditions with complete Z-selectivity using bis(trifluoroethyl) phosphonates and LiCl, DBU in THF. The use of the corresponding dimethyl phosphonates resulted in a mixture off and Z-configurated products, the ratio of which was found to depend on the size of the ester group. (C) 1997, Elsevier Science Ltd.
• Kolter, Thomas; Dahl, Christina; Giannis, Athanassios, Liebigs Annalen, 1995, # 4, p. 625 - 630
  作者：Kolter, Thomas、Dahl, Christina、Giannis, Athanassios

  DOI：——

  日期：——
• [EN] METHODS FOR PREPARING DIAZONAMIDES<br/>[FR] PROCÉDÉS POUR PRÉPARER DES DIAZONAMIDES
  申请人：JOYANT PHARMACEUTICALS INC

  公开号：WO2008154441A1

  公开（公告）日：2008-12-18

  [EN] This invention relates to novel macrocyclic lactams intermediates useful for the preparation of diazonamide analogs. This invention also relates to a novel electrochemical oxidative cyclization for the preparation of such macrocyclic lactams, and their further elucidation to provide diazonamide analogs.
  [FR] La présente invention concerne des intermédiaires lactames macrocycliques novateurs utilisés pour la préparation d'analogues de diazonamide. L'invention concerne également une cyclisation oxydante électrochimique novatrice pour la préparation de tels lactames macrocycliques, et leur élucidation poussée pour former des analogues de diazonamide.
• Kolter, Thomas; Klein, Annegret; Giannis, Athanassios, Angewandte Chemie, 1992, vol. 104, # 10, p. 1394 - 1395
  作者：Kolter, Thomas、Klein, Annegret、Giannis, Athanassios

  DOI：——

  日期：——
• Barbier-type allylation of chiral α-aminoaldehydes: Dependence of the stereochemical outcome on metal and allylic halide
  作者：Frank Rübsam、Stephan Seck、Athanassios Giannis

  DOI：10.1016/s0040-4020(97)00050-1

  日期：1997.2

  The chiral beta-hydroxy-alpha-aminoaldehydes of type 1 react smoothly with allyl-, 3,3-dimethylallyl bromide and 2-bromo-cyclohexene in the presence of tin or zinc dust to give the homoallylic alcohols of type 3. For the first time it is shown that the diastereoselectivity in in the Barbier reaction can be influenced by the choice of metal and/or allylic halide. (C) 1997 Published by Elsevier Science Ltd.