methyl (3aS,4R,6R,6aS)-4-amino-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate | 153796-90-8

• 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: methyl (3aS,4R,6R,6aS)-4-amino-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate
• CAS: 153796-90-8
• 化学式: C₁₄H₂₃NO₇
• 分子量: 317.339
• InChiKey: IUXMUIJADQWPSA-BDKTZFNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (3aS,4R,6R,6aS)-4-amino-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate 在 钯 氢气 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 18.0h， 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-galacto-heptono-1,5-lactone 在 钯 氢气 、 溴 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 methyl (3aS,4R,6R,6aS)-4-amino-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate
  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

文献信息

• Tri- and tetra-peptides incorporating an α-amino acid at the anomeric position of mannofuranose
  作者：Juan C. Estevez、Ramon J. Estevez、Helen Ardron、Mark R. Wormald、David Brown、George W.J. Fleet

  DOI：10.1016/s0040-4039(00)78525-x

  日期：1994.11

  The first examples of peptides containing an alpha-amino acid residue in which the alpha-carbon is also the anomeric position of a carbohydrate are described.
• 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.
• A General Synthetic Route to Anomeric .alpha.-Azido and .alpha.-Amino Acids and Formal Synthesis of (+)-Hidantocidin
  作者：Alessandro Dondoni、Marie-Christine Scherrmann、Alberto Marra、Jean-Louis Delepine

  DOI：10.1021/jo00103a057

  日期：1994.12
• 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.