(3aS,4R,5S,7aR)-5-azido-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol | 172017-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,5S,7aR)-5-azido-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
• CAS: 172017-19-5
• 化学式: C₉H₁₃N₃O₃
• 分子量: 211.221
• InChiKey: VUTBBQXJBGVXOG-LXGUWJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,4R,5S,7aR)-5-azido-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol 、 丙炔酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到(5aR,6R,7R,9aS)-6,7-(2,2-dimethyl-1,3-dioxolane)-5a,6,7,9a-tetrahydro-4H-[1,2,3]triazolo[5,1-c][1,4]benzoxazin-4-one
  参考文献：
  名称：

  Click chemistry and biocatalysis for the preparation of pancratistatin analogs

  摘要：

  Tricyclic compounds that are advanced precursors for the synthesis of analogs of the antitumoral alkaloid pancratistatin were prepared by a short sequence that involved enzymatic dihydroxylation, epoxidation, and intramolecular Huisgen cycloaddition. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.084
• 作为产物：
  描述：

  [3aR-(3aα,5aβ,6aβ,6bα)]-3a,5a,6a,6b-四氢-2,2-二甲基环氧乙烯并[e]-1,3-苯并间二氧杂环戊烯 在 sodium azide 、 氯化铵 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.0h， 以95%的产率得到(3aS,4R,5S,7aR)-5-azido-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
  参考文献：
  名称：

  Chemoenzymatic synthesis of glycosyl-deoxyinositol derivatives. First example of a fagopyritol β-analogue containing an aminoinositol unit

  摘要：

  The first synthesis of two fagopyritol beta-analogues (beta-D-galactopyranosyl-(1' -> 1)-conduramine F-4 and beta-D-galactopyranosyl-(1' -> 3)-4-aminodeoxy-L-chiro-inositol) has been accomplished by a chemoenzymatic route in satisfactory yields. The key step of the synthesis is the TMSOTf-promoted glycosylation reaction of a deoxyconduritol derivative. The methodology is amenable to scale-up and expandable to the preparation of other pseudofagopyritols. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.011

文献信息

• Chemoenzymatic synthesis of glycosyl-deoxyinositol derivatives. First example of a fagopyritol β-analogue containing an aminoinositol unit
  作者：Ana Bellomo、Julia B. Bonilla、Javier López-Prados、Manuel Martín-Lomas、David Gonzalez

  DOI：10.1016/j.tetasy.2009.08.011

  日期：2009.9

  The first synthesis of two fagopyritol beta-analogues (beta-D-galactopyranosyl-(1' -> 1)-conduramine F-4 and beta-D-galactopyranosyl-(1' -> 3)-4-aminodeoxy-L-chiro-inositol) has been accomplished by a chemoenzymatic route in satisfactory yields. The key step of the synthesis is the TMSOTf-promoted glycosylation reaction of a deoxyconduritol derivative. The methodology is amenable to scale-up and expandable to the preparation of other pseudofagopyritols. (C) 2009 Elsevier Ltd. All rights reserved.
• Click chemistry and biocatalysis for the preparation of pancratistatin analogs
  作者：Victoria de la Sovera、Ana Bellomo、David Gonzalez

  DOI：10.1016/j.tetlet.2010.11.084

  日期：2011.1

  Tricyclic compounds that are advanced precursors for the synthesis of analogs of the antitumoral alkaloid pancratistatin were prepared by a short sequence that involved enzymatic dihydroxylation, epoxidation, and intramolecular Huisgen cycloaddition. (c) 2010 Elsevier Ltd. All rights reserved.