4,5,6-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo-septanosyl azide | 944478-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,5,6-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo-septanosyl azide
• 英文别名: (2R,3R,5R,6S,7R)-2-azido-5,6-bis(phenylmethoxy)-7-(phenylmethoxymethyl)oxepan-3-ol
• CAS: 944478-39-1
• 化学式: C₂₈H₃₁N₃O₅
• 分子量: 489.571
• InChiKey: YNMBBJGQQRFRIQ-VNFNVIIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,5,6-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo-septanosyl azide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 28.0h， 生成 1-(3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole-4,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Synthesis of substituted septanosyl-1,2,3-triazoles

  摘要：

  A carbohydrate-based oxepine, derived from 2-deoxy-D-arabino-hexopyranose, was used to prepare a family of septanosyl-1,2,3-triazoles in four steps. DMDO mediated epoxidation of the oxepine followed by trapping of the intermediate 1,2-anhydroseptanose by sodium azide gave the beta-substituted glycosyl azide. The septanosyl azide was then reacted with a number of alkynes under thermal Huisgen or copper(I) mediated reaction conditions. Hydrogenolysis of benzyl protecting groups gave substituted septanosyl-1,2,3-triazoles. The new septanose-based structures were then evaluated as potential glycosidase inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.026
• 作为产物：
  描述：

  1,6-anhydro-4,5,7-tri-O-benzyl-2,3-dideoxy-D-glucosept-1-enitol 在 sodium azide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以22%的产率得到4,5,6-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo-septanosyl azide
  参考文献：
  名称：

  Synthesis of substituted septanosyl-1,2,3-triazoles

  摘要：

  A carbohydrate-based oxepine, derived from 2-deoxy-D-arabino-hexopyranose, was used to prepare a family of septanosyl-1,2,3-triazoles in four steps. DMDO mediated epoxidation of the oxepine followed by trapping of the intermediate 1,2-anhydroseptanose by sodium azide gave the beta-substituted glycosyl azide. The septanosyl azide was then reacted with a number of alkynes under thermal Huisgen or copper(I) mediated reaction conditions. Hydrogenolysis of benzyl protecting groups gave substituted septanosyl-1,2,3-triazoles. The new septanose-based structures were then evaluated as potential glycosidase inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.026

文献信息

• Synthesis of substituted septanosyl-1,2,3-triazoles
  作者：Steve Castro、Emily C. Cherney、Nicole L. Snyder、Mark W. Peczuh

  DOI：10.1016/j.carres.2007.03.026

  日期：2007.7

  A carbohydrate-based oxepine, derived from 2-deoxy-D-arabino-hexopyranose, was used to prepare a family of septanosyl-1,2,3-triazoles in four steps. DMDO mediated epoxidation of the oxepine followed by trapping of the intermediate 1,2-anhydroseptanose by sodium azide gave the beta-substituted glycosyl azide. The septanosyl azide was then reacted with a number of alkynes under thermal Huisgen or copper(I) mediated reaction conditions. Hydrogenolysis of benzyl protecting groups gave substituted septanosyl-1,2,3-triazoles. The new septanose-based structures were then evaluated as potential glycosidase inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.