2-Amino-2-deoxy-3,4-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone | 172987-03-0

• 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: 2-Amino-2-deoxy-3,4-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone
• 英文别名: (3aR,4R,7S,7aR)-7-amino-4-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 172987-03-0
• 化学式: C₁₀H₁₇NO₆
• 分子量: 247.248
• InChiKey: AEWIOWNAIDXHQG-UOLFYFMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Amino-2-deoxy-3,4-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 作用下， 以 乙腈 为溶剂， 生成 (1S,2S,6S,7R,11R)-1-Amino-11-hydroxymethyl-4,4-dimethyl-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undecan-9-one
  参考文献：
  名称：

  Spirodiketopiperazines at the anomeric position of mannopyranose: Novel N- linked glycopeptides incorporating an α- amino acid at the anomeric position of mannopyranose

  摘要：

  The first synthesis of a spirodiketopiperazine at the anomeric carbon of a pyranose sugar is described; an N-acylated bicyclic amino [2.2.2] lactone provides access to a new class of glycopeptide analogues of pyranoses and determines the anomeric configuration of the spirodiketopiperazine. The mannopyranose may be equilibrated to the more stable furanose form.

  DOI：

  10.1016/0040-4039(95)01732-w
• 作为产物：
  描述：

  2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone 在 钯 水 、 氢气 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 生成 2-Amino-2-deoxy-3,4-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone
  参考文献：
  名称：

  Spirodiketopiperazines at the anomeric position of mannopyranose: Novel N- linked glycopeptides incorporating an α- amino acid at the anomeric position of mannopyranose

  摘要：

  The first synthesis of a spirodiketopiperazine at the anomeric carbon of a pyranose sugar is described; an N-acylated bicyclic amino [2.2.2] lactone provides access to a new class of glycopeptide analogues of pyranoses and determines the anomeric configuration of the spirodiketopiperazine. The mannopyranose may be equilibrated to the more stable furanose form.

  DOI：

  10.1016/0040-4039(95)01732-w

文献信息

• Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose
  作者：Daniel D. Long、Richard J. Tennant-Eyles、Juan C. Estevez、Mark R. Wormald、Raymond A. Dwek、Martin D. Smith、George W. J. Fleet

  DOI：10.1039/b009940f

  日期：——

  an anomeric α-amino acid component is described. An N-acylated bicyclic [2.2.2] lactone, formed via an oxidative ring closure, provides access to a new class of glycopeptide analogues of D-mannopyranose and determines the anomeric configuration of compounds derived therefrom. The mannopyranose diketopiperazine may be equilibrated to the more stable furanose form under basic conditions; in general,

  描述了一种合成具有异头α-氨基酸组分的D-甘露吡喃糖衍生物的方法。一个Ñ -acylated双环[2.2.2]内酯通过氧化闭环形成，提供了进入新类别的糖肽 类似物 D-甘露吡喃糖并确定由此衍生的化合物的异头构型。这甘露吡喃糖二酮哌嗪在基本条件下可以平衡为更稳定的呋喃糖形式；一般来说，甘露吡喃糖 在异头位置含有α-氨基酸部分的衍生物比甘露呋喃糖异构体的稳定性差。