(3S,4S,5S)-3-[N-(tert-Butoxycarbonyl)amino]-5-hydroxyhexano-4-lactone | 178976-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4S,5S)-3-[N-(tert-Butoxycarbonyl)amino]-5-hydroxyhexano-4-lactone
• 英文别名: tert-butyl N-[(2S,3S)-2-[(1S)-1-hydroxyethyl]-5-oxooxolan-3-yl]carbamate
• CAS: 178976-46-0
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: UQXYPKOMLXDGIV-ACLDMZEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S,5S)-3-[N-(tert-Butoxycarbonyl)amino]-5-hydroxyhexano-4-lactone 在 盐酸 、 甲醇 、 二异丁基氢化铝 作用下， 生成 六碳氨糖盐酸盐
  参考文献：
  名称：

  Asymmetric synthesis of methyl α-L-daunosaminide hydrochloride

  摘要：

  Methyl alpha-L-daunosaminide hydrochloride was synthesised in five steps from methyl (E,E)-hexa-2,4-dienoate, via the conjugate addition of (R)-lithium N-benzyl-alpha-methylbenzylamide, and osmium tetroxide catalysed dihydroxylation of the resulting adduct. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00141-3
• 作为产物：
  描述：

  (2S,3S)-2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxooxolane-3-carboxylic acid 在 二苯基磷酸 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.0h， 生成 (3S,4S,5S)-3-[N-(tert-Butoxycarbonyl)amino]-5-hydroxyhexano-4-lactone
  参考文献：
  名称：

  A New Route to 3-Amino Sugars. A Concise Synthesis of l-Daunosamine and d-Ristosamine Derivatives

  摘要：

  An asymmetric aldol strategy has been developed for the synthesis of L-daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O-TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two-step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similarly, lactone 32 was converted to N-benzoylristosamide 42 with an overall yield of 18% starting from 12.

  DOI：

  10.1021/jo970576f

文献信息

• Syntheses of derivatives of L-daunosamine and its C-3 epimer employing as the key step the asymmetric conjugate addition of a homochiral lithium amide to tert-butyl (E,E )-hexa-2,4-dienoate
  作者：Stephen G. Davies、G. Darren Smyth、Ann M. Chippindale

  DOI：10.1039/a907017f

  日期：——

  The highly diastereoselective asymmetric conjugate addition of lithium (R)-N-benzyl-α-methylbenzylamide to methyl or tert-butyl (E,E)-hexa-2,4-dienoate, followed by osmium tetroxide-catalysed dihydroxylation of the resulting adducts, provides a concise route to methyl L-daunosaminide hydrochloride and methyl 3-epi-D-daunosaminide hydrochloride, a strategy which is applicable to the synthesis of either

  锂（R）-N-苄基-α-甲基苄基酰胺的高度非对映选择性不对称共轭加成至（E，E）-己二酸-6,2-二烯酸叔丁酯或叔丁基，然后四氧化os催化所得加合物的二羟基化，提供了获得甲基L-柔红酰胺盐酸盐和甲基3- epi - D的简洁途径-达柔诺胺盐酸盐，该策略适用于这些化合物的任一对映异构体的合成。关键的二羟基化反应的选择性可以通过采用Sharpless不对称二羟基化方案来显着提高。由于低选择性或需要过多的步骤，使用碘代内酯化或碘代环氨基甲酸酯化反应作为关键步骤的可能替代策略被发现不太令人满意。
• A New Route to 3-Amino Sugars. A Concise Synthesis of <scp>l</scp>-Daunosamine and <scp>d</scp>-Ristosamine Derivatives
  作者：Mukund P. Sibi、Jianliang Lu、Jessica Edwards

  DOI：10.1021/jo970576f

  日期：1997.8.1

  An asymmetric aldol strategy has been developed for the synthesis of L-daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O-TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two-step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similarly, lactone 32 was converted to N-benzoylristosamide 42 with an overall yield of 18% starting from 12.
• Asymmetric synthesis of methyl α-L-daunosaminide hydrochloride
  作者：Stephen G Davies、G Darren Smyth

  DOI：10.1016/0957-4166(96)00141-3

  日期：1996.5

  Methyl alpha-L-daunosaminide hydrochloride was synthesised in five steps from methyl (E,E)-hexa-2,4-dienoate, via the conjugate addition of (R)-lithium N-benzyl-alpha-methylbenzylamide, and osmium tetroxide catalysed dihydroxylation of the resulting adduct. Copyright (C) 1996 Elsevier Science Ltd