(2S,3S)-N-allyl-N-tert-butoxycarbonyl-3-amino-5-hexen-1,2-diol | 417726-32-0

• 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: (2S,3S)-N-allyl-N-tert-butoxycarbonyl-3-amino-5-hexen-1,2-diol
• 英文别名: tert-butyl N-[(2S,3S)-1,2-dihydroxyhex-5-en-3-yl]-N-prop-2-enylcarbamate
• CAS: 417726-32-0
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: YFCYCCYQKVJYEP-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-N-allyl-N-tert-butoxycarbonyl-3-amino-5-hexen-1,2-diol 在 Grubbs catalyst first generation sodium chlorite 、 sodium periodate 、 sodium dihydrogenphosphate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 (S)-N-BOC-1,2,3,6-四氢-2-吡啶羧酸
  参考文献：
  名称：

  Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain

  摘要：

  New enantioselective syntheses of N-protected baikiain and pipecolic acid have been developed. The starting material is 2,3-epoxy-5-hexen-1-ol (4) readily available in high ee by Sharpless epoxidation. The regio- and stereoselective epoxide ring-opening by allylamine afforded a doubly unsaturated amine that was converted into a carbamate (Boc) and submitted to ring-closing metathesis. The resulting cyclic amino diol 6 is a key intermediate that was converted into N-Boc-baikiain and several pipecolic acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02271-7
• 作为产物：
  描述：

  ((2R,3R)-3-allyloxiran-2-yl)methanol 在 lithium perchlorate 、 碳酸氢钠 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (2S,3S)-N-allyl-N-tert-butoxycarbonyl-3-amino-5-hexen-1,2-diol
  参考文献：
  名称：

  Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain

  摘要：

  New enantioselective syntheses of N-protected baikiain and pipecolic acid have been developed. The starting material is 2,3-epoxy-5-hexen-1-ol (4) readily available in high ee by Sharpless epoxidation. The regio- and stereoselective epoxide ring-opening by allylamine afforded a doubly unsaturated amine that was converted into a carbamate (Boc) and submitted to ring-closing metathesis. The resulting cyclic amino diol 6 is a key intermediate that was converted into N-Boc-baikiain and several pipecolic acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02271-7

文献信息

• Asymmetric Synthesis ofcis-4- andtrans-3-Hydroxypipecolic Acids
  作者：Carlos Alegret、Xavier Ginesta、Antoni Riera

  DOI：10.1002/ejoc.200701103

  日期：2008.4

  Enantioselective syntheses of cis-4- and trans-3-hydroxypipecolic acids from 2,3-epoxy-5-hexen-1-ol (7) are described. Regioselective C-3 or C-2 ring opening of the epoxide by the appropriate nitrogen nucleophile is the key step in each route. As enantiomerically enriched epoxy alcohols are readily available in any configuration by Sharpless epoxidation, both enantiomers are equally accessible. This

  描述了从 2,3-epoxy-5-hexen-1-ol (7) 合成 cis-4- 和 trans-3-hydroxypipecolic 酸的对映选择性合成。通过适当的氮亲核试剂对环氧化物进行区域选择性 C-3 或 C-2 开环是每条路线中的关键步骤。由于对映体富集的环氧醇可通过 Sharpless 环氧化以任何构型轻松获得，因此两种对映体都可同样获得。这种方法也被用来合成天然产物黄芩苷和重要的合成中间体反式-3-羟基-2-羟甲基哌啶。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)