(3aR,4R,7S,7aR)-7-amino-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one | 153796-88-4

• 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: (3aR,4R,7S,7aR)-7-amino-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 153796-88-4
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: NNPBGHYXBDJMPL-ZOZBQHSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,4R,7S,7aR)-7-amino-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one 在 钯 氢气 、 溴 、 sodium acetate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 42.0h， 生成 1-(S)-(3',6'-diketopiperazine)-1,4-anhydro-2,3:5,6-di-O-isopropylidene-D-mannose
  参考文献：
  名称：

  Spirodiketopiperazines of mannofuranose: carbopeptoid α-amino acid esters at the anomeric position of mannofuranose

  摘要：

  Epimeric mannofuranose anomeric aminoesters are prepared from readily available azidolactones and can act as building blocks for the incorporation of mannofuranose units into peptide chains [carbopeptoids]; alternative acylating conditions allow either rapid acylation of the more stable but kinetically hindered amine or reaction with the less hindered but less stable amine to allow control of the anomeric configuration of the products. This is exemplified by coupling of the aminoesters with glycine derivatives to give dipeptide equivalents, and subsequent cyclization to spiro diketopiperazines, Anomers with the nitrogen function cis to the 2,3-diol are more stable than those with nitrogen trans; mannofuranose derivatives are more stable than the mannopyranose isomers. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00206-7
• 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 氢气 作用下， 以 乙酸乙酯 为溶剂， 以94%的产率得到(3aR,4R,7S,7aR)-7-amino-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
  参考文献：
  名称：

  Anomeric spirohydantoins of mannofuranose: Approaches to novel anomeric amino acids by an oxidative ring contraction

  摘要：

  Bromine-induced oxidative ring contraction of an alpha-amino-delta-lactone gave a mixture of alpha-aminotetrahydrofurancarboxylic esters which may allow the preparation of stable amino acid derivatives at the anomeric position of mannofuranose. The synthesis of N-phenylhydantoins at the anomeric position of mannofuranose is reported.

  DOI：

  10.1016/s0040-4039(00)61745-8

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。
• Anomeric spirohydantoins of mannofuranose: Approaches to novel anomeric amino acids by an oxidative ring contraction
  作者：Jonathan W. Burton、Jong Chan Son、Antony J. Fairbanks、Sik-man S. Choi、Helen Taylor、David J. Watkin、Bryan G. Winchester、George W.J. Fleet

  DOI：10.1016/s0040-4039(00)61745-8

  日期：1993.9

  Bromine-induced oxidative ring contraction of an alpha-amino-delta-lactone gave a mixture of alpha-aminotetrahydrofurancarboxylic esters which may allow the preparation of stable amino acid derivatives at the anomeric position of mannofuranose. The synthesis of N-phenylhydantoins at the anomeric position of mannofuranose is reported.
• Spirodiketopiperazines at the anomeric position of mannopyranose: Novel N- linked glycopeptides incorporating an α- amino acid at the anomeric position of mannopyranose
  作者：Juan C. Estevez、Daniel D. Long、Mark R. Wormald、Raymond A. Dwek、George W.J. Fleet

  DOI：10.1016/0040-4039(95)01732-w

  日期：1995.11

  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.
• Spirodiketopiperazines of mannofuranose: carbopeptoid α-amino acid esters at the anomeric position of mannofuranose
  作者：Juan C Estevez、Jonathan W Burton、Ramon J Estevez、Helen Ardron、Mark R Wormald、Raymond A Dwek、David Brown、George W.J Fleet

  DOI：10.1016/s0957-4166(98)00206-7

  日期：1998.6

  Epimeric mannofuranose anomeric aminoesters are prepared from readily available azidolactones and can act as building blocks for the incorporation of mannofuranose units into peptide chains [carbopeptoids]; alternative acylating conditions allow either rapid acylation of the more stable but kinetically hindered amine or reaction with the less hindered but less stable amine to allow control of the anomeric configuration of the products. This is exemplified by coupling of the aminoesters with glycine derivatives to give dipeptide equivalents, and subsequent cyclization to spiro diketopiperazines, Anomers with the nitrogen function cis to the 2,3-diol are more stable than those with nitrogen trans; mannofuranose derivatives are more stable than the mannopyranose isomers. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.