(S)-((2'S,3'R,4'S,6'S)-1'-hydroxy-2',4',6'-trimethyldodecan-3'-yl) 2-(tert-butoxycarbonylamino)propanoate | 1233512-13-4

• 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: (S)-((2'S,3'R,4'S,6'S)-1'-hydroxy-2',4',6'-trimethyldodecan-3'-yl) 2-(tert-butoxycarbonylamino)propanoate
• CAS: 1233512-13-4
• 化学式: C₂₃H₄₅NO₅
• 分子量: 415.614
• InChiKey: PTJOTJRRQBDNCX-VYJAJWGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  29.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-((2'S,3'R,4'S,6'S)-1'-hydroxy-2',4',6'-trimethyldodecan-3'-yl) 2-(tert-butoxycarbonylamino)propanoate 在 sodium periodate 、 rhodium(III) chloride hydrate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.0h， 生成 (5S,8S,11S,14S)-((2'R,3'R,4'S,6'S)-1'-(2"-(benzyloxy)-2"-oxoethylamino)-2', 4',6'-trimethyl-1'-oxododecan-3'-yl) 8-isobutyl-5-isopropyl-11,14-dimethyl-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oate
  参考文献：
  名称：

  Asymmetric synthesis of emericellamide B

  摘要：

  Asymmetric total synthesis of emericellamide B (9.4%, 17 longest linear steps) is detailed in this report. In this synthetic route, the highly methylated (2R,3R,4S,6S)-3-hydroxy-2,4,6-trimethyldodecanoic acid (HTMD) unit was effectively prepared through the asymmetric methylation, Wittig and Horner-Wadsworth-Emmons reaction. Moreover, pentafluorophenyl diphenylphophinate (FDPP) proved to be an effective condensation reagent for the macrolactamization between C14 and C18. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.07.023
• 作为产物：
  描述：

  (2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal 在 盐酸 、 甲醇 、 sodium tetrahydroborate 、 锂硼氢 、 正丁基锂 、 草酰氯 、 nickel(II) chloride hexahydrate 、 lithium hydroxide monohydrate 、 palladium 10% on activated carbon 、 氢气 、 sodium hexamethyldisilazane 、 三甲基乙酰氯 、 sodium hydride 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， -78.0~60.0 ℃ 、101.33 kPa 条件下， 反应 23.75h， 生成 (S)-((2'S,3'R,4'S,6'S)-1'-hydroxy-2',4',6'-trimethyldodecan-3'-yl) 2-(tert-butoxycarbonylamino)propanoate
  参考文献：
  名称：

  Asymmetric synthesis of emericellamide B

  摘要：

  Asymmetric total synthesis of emericellamide B (9.4%, 17 longest linear steps) is detailed in this report. In this synthetic route, the highly methylated (2R,3R,4S,6S)-3-hydroxy-2,4,6-trimethyldodecanoic acid (HTMD) unit was effectively prepared through the asymmetric methylation, Wittig and Horner-Wadsworth-Emmons reaction. Moreover, pentafluorophenyl diphenylphophinate (FDPP) proved to be an effective condensation reagent for the macrolactamization between C14 and C18. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.07.023

文献信息

• Application of desymmetrization protocol for the formal total synthesis of emericellamide B
  作者：Debendra K. Mohapatra、Sk. Samad Hossain、Santu Dhara、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.04.015

  日期：2010.6

  A highly convergent formal total synthesis of emericellamide B, a 19-membered antibacterial depsipeptide is described. The key feature of the strategy is the generation of four stereogenic centers from a bicyclic precursor via desymmetrization technique and utilization for emericellamide B and related natural product synthesis. (C) 2010 Elsevier Ltd. All tights reserved.