methyl (3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[[2-(phenylmethoxycarbonylamino)acetyl]amino]-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate | 161007-87-0

• 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: methyl (3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[[2-(phenylmethoxycarbonylamino)acetyl]amino]-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate
• CAS: 161007-87-0
• 化学式: C₂₄H₃₂N₂O₁₀
• 分子量: 508.525
• InChiKey: XRBLZEFJUFMESV-UGUXIJLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[[2-(phenylmethoxycarbonylamino)acetyl]amino]-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate 在 盐酸 、 亚硝酸特丁酯 、 一水合肼 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 {[(3aS,4R,6R,6aS)-4-(2-Benzyloxycarbonylamino-acetylamino)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-amino}-acetic acid methyl ester
  参考文献：
  名称：

  Tri- and tetra-peptides incorporating an α-amino acid at the anomeric position of mannofuranose

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)78525-x
• 作为产物：
  描述：

  (3aR,4R,7R,7aR)-7-Amino-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one 在 溴 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 methyl (3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[[2-(phenylmethoxycarbonylamino)acetyl]amino]-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

• Spirocyclic peptides at the anomeric position of mannofuranose
  作者：Juan C. Estevez、Helen Ardron、Mark R. Wormald、David Brown、George W.J. Fleet

  DOI：10.1016/s0040-4039(00)78526-1

  日期：1994.11

  The first syntheses of two diketopiperazine peptides containing an α-amino in which the α-carbon is also the anomeric carbon of a carbohydrate are described; studies on the kinetic and thermodynamic stability of the spirocyclic dipeptides are reported.

  描述了包含α-氨基的两个二酮哌嗪肽的第一合成，其中α-碳也是碳水化合物的异头碳；报道了螺环二肽的动力学和热力学稳定性的研究。