((3S,4S,7S)-7-Isobutyl-3-isopropyl-5,8,11-trioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-trien-4-yl)-carbamic acid tert-butyl ester | 220522-28-1

• 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: ((3S,4S,7S)-7-Isobutyl-3-isopropyl-5,8,11-trioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-trien-4-yl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3S,4S,7S)-7-(2-methylpropyl)-5,8,11-trioxo-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),12,15-trien-4-yl]carbamate
• CAS: 220522-28-1
• 化学式: C₂₅H₃₇N₃O₆
• 分子量: 475.585
• InChiKey: GIQYTHATDXBUDL-JBACZVJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((3S,4S,7S)-7-Isobutyl-3-isopropyl-5,8,11-trioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-trien-4-yl)-carbamic acid tert-butyl ester 在 吡啶 、 2,6-二甲基吡啶 、 2-硝基苯基丝氰酸酯 、 硼烷四氢呋喃络合物 、 三丁基膦 、 三氟甲磺酸三甲基硅酯 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,4S,7S,10Z)-4-amino-7-(2-methylpropyl)-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraene-5,8-dione
  参考文献：
  名称：

  Total synthesis of sanjoinine A (frangufoline)

  摘要：

  Sanjoinine A (1) was synthesized from a 14-membered cyclopeptide prepared from a Garner aldehyde derived from D-serine. The key steps in the synthesis were the catalytic asymmetric reduction of ketone 2(b) and the final removal of the Boc group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02278-3
• 作为产物：
  描述：

  [3S,4S,7S,11S]-(11-hydroxy-7-isobutyl-3-isopropyl-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(15),12(16),13-trien-4-yl)-carbamic acid tert-butyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到((3S,4S,7S)-7-Isobutyl-3-isopropyl-5,8,11-trioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-trien-4-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis of sanjoinine A (frangufoline)

  摘要：

  Sanjoinine A (1) was synthesized from a 14-membered cyclopeptide prepared from a Garner aldehyde derived from D-serine. The key steps in the synthesis were the catalytic asymmetric reduction of ketone 2(b) and the final removal of the Boc group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02278-3

文献信息

• Total synthesis of sanjoinine A (frangufoline)
  作者：Dong Xiao、Stephen P. East、Madeleine M. Joullié

  DOI：10.1016/s0040-4039(98)02278-3

  日期：1998.12

  Sanjoinine A (1) was synthesized from a 14-membered cyclopeptide prepared from a Garner aldehyde derived from D-serine. The key steps in the synthesis were the catalytic asymmetric reduction of ketone 2(b) and the final removal of the Boc group. (C) 1998 Elsevier Science Ltd. All rights reserved.