(3R,3aS,4S,6aS)-4-((R)-3-(benzyloxy)-2-methylpropyl)-dihydro-3a-hydroxy-6a-(hydroxymethyl)-1,3-dimethyl-1H-furo[3,4-b]pyrrole-2,6(3H,6aH)-dione | 955959-48-5

• 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: (3R,3aS,4S,6aS)-4-((R)-3-(benzyloxy)-2-methylpropyl)-dihydro-3a-hydroxy-6a-(hydroxymethyl)-1,3-dimethyl-1H-furo[3,4-b]pyrrole-2,6(3H,6aH)-dione
• 英文别名: (3R,3aS,4S,6aS)-3a-hydroxy-6a-(hydroxymethyl)-1,3-dimethyl-4-[(2R)-2-methyl-3-phenylmethoxypropyl]-3,4-dihydrofuro[3,4-b]pyrrole-2,6-dione
• CAS: 955959-48-5
• 化学式: C₂₀H₂₇NO₆
• 分子量: 377.437
• InChiKey: MWFGQIWOPFJHFP-RUTGWLNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,3aS,4S,6aS)-4-((R)-3-(benzyloxy)-2-methylpropyl)-dihydro-3a-hydroxy-6a-(hydroxymethyl)-1,3-dimethyl-1H-furo[3,4-b]pyrrole-2,6(3H,6aH)-dione 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 1,8-双二甲氨基萘 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 122.5h， 生成 (3R,4S,5R)-4-((1S,3R)-3-((benzyloxy)methyl)-1-methoxybutyl)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-5-((methoxymethoxy)methyl)-1,3-dimethylpyrrolidin-2-one
  参考文献：
  名称：

  Total Synthesis of Oxazolomycin A

  摘要：

  The first total synthesis of oxazolomycin A, a structurally novel oxazole polyene gamma-lactam/beta-lactone antibiotic, is described. Key features Include the stereocontrolled construction of the right-hand heterocyclic core by taking advantage of an In(III)-catalyzed Conia-ene type cyclization and the asymmetric synthesis of the left-hand segment starting with a Cinchona alkaloid-catalyzed cyclocondensation of an aldehyde with an acid chloride.

  DOI：

  10.1021/ol202306d
• 作为产物：
  描述：

  (3R,3aS,4S,6aR)-methyl 4-((R)-3-(benzyloxy)-2-methylpropyl)-hexahydro-3a-hydroxy-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate 在 草酰氯 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (3R,3aS,4S,6aS)-4-((R)-3-(benzyloxy)-2-methylpropyl)-dihydro-3a-hydroxy-6a-(hydroxymethyl)-1,3-dimethyl-1H-furo[3,4-b]pyrrole-2,6(3H,6aH)-dione
  参考文献：
  名称：

  Total Synthesis of Oxazolomycin A

  摘要：

  The first total synthesis of oxazolomycin A, a structurally novel oxazole polyene gamma-lactam/beta-lactone antibiotic, is described. Key features Include the stereocontrolled construction of the right-hand heterocyclic core by taking advantage of an In(III)-catalyzed Conia-ene type cyclization and the asymmetric synthesis of the left-hand segment starting with a Cinchona alkaloid-catalyzed cyclocondensation of an aldehyde with an acid chloride.

  DOI：

  10.1021/ol202306d

文献信息

• Total Synthesis of Neooxazolomycin
  作者：Evans Otieno Onyango、Joji Tsurumoto、Naoko Imai、Keisuke Takahashi、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1002/anie.200702229

  日期：2007.9.3
• Stereoselective synthesis of the right-hand cores of 16-methylated oxazolomycins
  作者：Kohei Eto、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1016/j.tet.2017.12.036

  日期：2018.2

  The right-hand heterocyclic cores of oxazolomycins having either 16R or 16S-methyl group configurations on the beta-lactones were stereoselectively synthesized from the common intermediate utilized for our previous syntheses of neooxazolomycin and oxazolomycin A. In addition, the right-hand segment required for the synthesis of KSM-2690 and lajollamycin members was also synthesized in a stereo-selective manner. (C) 2017 Elsevier Ltd. All rights reserved.
• Total Synthesis of Oxazolomycin A
  作者：Kohei Eto、Madoka Yoshino、Keisuke Takahashi、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1021/ol202306d

  日期：2011.10.7

  The first total synthesis of oxazolomycin A, a structurally novel oxazole polyene gamma-lactam/beta-lactone antibiotic, is described. Key features Include the stereocontrolled construction of the right-hand heterocyclic core by taking advantage of an In(III)-catalyzed Conia-ene type cyclization and the asymmetric synthesis of the left-hand segment starting with a Cinchona alkaloid-catalyzed cyclocondensation of an aldehyde with an acid chloride.