(3aS,4R,6R,6aS)-4-(2-Benzyloxycarbonylamino-acetylamino)-6-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester | 161086-23-3

• 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: (3aS,4R,6R,6aS)-4-(2-Benzyloxycarbonylamino-acetylamino)-6-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester
• CAS: 161086-23-3
• 化学式: C₂₁H₂₈N₂O₁₀
• 分子量: 468.461
• InChiKey: VRCXBKULZIMFDC-XCUUDAFNSA-N

物化性质

• 沸点：
  709.014±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.412±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  161.88
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6R,6aS)-4-(2-Benzyloxycarbonylamino-acetylamino)-6-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester 在 对甲苯磺酸 、 一水合肼 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 {[(3aS,4R,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydrazinocarbonyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylcarbamoyl]-methyl}-carbamic acid benzyl 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 甲醇 、 溴 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 (3aS,4R,6R,6aS)-4-(2-Benzyloxycarbonylamino-acetylamino)-6-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester
  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