tert-butyl N-[(2R)-1-(methoxymethoxy)-2-methyl-3-oxopropan-2-yl]carbamate | 1380501-15-4

• 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: tert-butyl N-[(2R)-1-(methoxymethoxy)-2-methyl-3-oxopropan-2-yl]carbamate
• CAS: 1380501-15-4
• 化学式: C₁₁H₂₁NO₅
• 分子量: 247.291
• InChiKey: JKGIZJISSQRAPU-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R)-1-(methoxymethoxy)-2-methyl-3-oxopropan-2-yl]carbamate 在 bis(N-tert-butylsalicylaldiminato)copper(II) 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 (4R,5R,6R)-5-hydroxy-6-(hydroxymethyl)-6-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
  参考文献：
  名称：

  Efficient total synthesis of manzacidin B

  摘要：

  The highly diastereoselective synthesis of the marine natural product, (-)-manzacidin B, is described. A novel copper-catalyzed aldol reaction of the alpha-methylserine-derived aldehyde with an isocyanoacetate possessing (1R)-camphorsultam as the chiral auxiliary proceeded in a highly diastereoselective manner to give the (4R,5R,6R)-adduct, which was converted into manzacidin B in a few steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.042
• 作为产物：
  描述：

  (R)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxypropanoic acid methyl ester 在 锂硼氢 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 tert-butyl N-[(2R)-1-(methoxymethoxy)-2-methyl-3-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Efficient total synthesis of manzacidin B

  摘要：

  The highly diastereoselective synthesis of the marine natural product, (-)-manzacidin B, is described. A novel copper-catalyzed aldol reaction of the alpha-methylserine-derived aldehyde with an isocyanoacetate possessing (1R)-camphorsultam as the chiral auxiliary proceeded in a highly diastereoselective manner to give the (4R,5R,6R)-adduct, which was converted into manzacidin B in a few steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.042

文献信息

• Efficient total synthesis of manzacidin B
  作者：Tetsuro Shinada、Kentaro Oe、Yasufumi Ohfune

  DOI：10.1016/j.tetlet.2012.04.042

  日期：2012.6

  The highly diastereoselective synthesis of the marine natural product, (-)-manzacidin B, is described. A novel copper-catalyzed aldol reaction of the alpha-methylserine-derived aldehyde with an isocyanoacetate possessing (1R)-camphorsultam as the chiral auxiliary proceeded in a highly diastereoselective manner to give the (4R,5R,6R)-adduct, which was converted into manzacidin B in a few steps. (C) 2012 Elsevier Ltd. All rights reserved.