6-azido-6-deoxy-2,3-O-isopropylidene-D-mannono-1,4-lactone | 201340-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-6-deoxy-2,3-O-isopropylidene-D-mannono-1,4-lactone
• 英文别名: (3aS,6R,6aS)-6-[(1R)-2-azido-1-hydroxyethyl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 201340-96-7
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: FNXNTPRTPCHPDZ-JWXFUTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-azido-6-deoxy-2,3-O-isopropylidene-D-mannono-1,4-lactone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 18.0h， 以68.8%的产率得到(3aS,7R,8R,8aS)-7,8-二羟基-2,2-二甲基六氢-4H-[1,3]二氧杂环戊并[4,5-c]氮杂卓-4-酮
  参考文献：
  名称：

  Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-glucitol)

  摘要：

  Syntheses of 1,6-dideoxy-1,6-imino-D-mannitol (D-mannoazepane) (1) and 1,6-dideoxy-1,6-imino-D-glucitol (D-glucoazepane) (3) from D-isoascorbic acid and D-glucono-1,5-lactone, respectively, are described. The key step in both routes involved reductive aminative 1,6-cyclization with retention of configurations to give the corresponding lactams, which were subsequently reduced to afford compounds 1 and 3 in 24 and 28.5%, overall yield, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00757-3
• 作为产物：
  描述：

  D-甘露糖-1,4-内酯 在 叠氮化锂 、 四溴化碳 、 对甲苯磺酸 、 溶剂黄146 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 6-azido-6-deoxy-2,3-O-isopropylidene-D-mannono-1,4-lactone
  参考文献：
  名称：

  Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-glucitol)

  摘要：

  Syntheses of 1,6-dideoxy-1,6-imino-D-mannitol (D-mannoazepane) (1) and 1,6-dideoxy-1,6-imino-D-glucitol (D-glucoazepane) (3) from D-isoascorbic acid and D-glucono-1,5-lactone, respectively, are described. The key step in both routes involved reductive aminative 1,6-cyclization with retention of configurations to give the corresponding lactams, which were subsequently reduced to afford compounds 1 and 3 in 24 and 28.5%, overall yield, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00757-3

文献信息

• Mixed sugar–nylon 14-, 28- and 42-membered ring macrocyclic lactams
  作者：Benjamin A. Mayes、Andrew R. Cowley、Christopher W.G. Ansell、George W.J. Fleet

  DOI：10.1016/j.tetlet.2003.10.105

  日期：2004.1

  Hydrogenation of linear ω-azido-pentafluorophenyl esters from mixed oligomers of 6-amino-6-deoxy-d-galactonic acid (or 6-amino-6-deoxy-d-mannonic acid) and 6-aminohexanoic acid gives cyclic peptides containing 14-, 28- and 42-membered ring lactams. Hydrogenation of a tetrameric peptide derived from ε-amino acids gave a 28-membered ring lactam in 79% yield.

  从6-氨基-6-脱氧-d-半乳糖酸（或6-氨基-6-脱氧-d-甘露酸）和6-氨基己酸的混合低聚物中氢化线性ω-叠氮基-五氟苯基酯，得到的环肽为14 -，28-和42-元环内酰胺。衍生自ε-氨基酸的四聚体肽的氢化反应产生28元环内酰胺，产率为79％。
• Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-glucitol)
  作者：Cosam C Joseph、Henk Regeling、Binne Zwanenburg、Gordon J.F Chittenden

  DOI：10.1016/s0040-4020(02)00757-3

  日期：2002.8

  Syntheses of 1,6-dideoxy-1,6-imino-D-mannitol (D-mannoazepane) (1) and 1,6-dideoxy-1,6-imino-D-glucitol (D-glucoazepane) (3) from D-isoascorbic acid and D-glucono-1,5-lactone, respectively, are described. The key step in both routes involved reductive aminative 1,6-cyclization with retention of configurations to give the corresponding lactams, which were subsequently reduced to afford compounds 1 and 3 in 24 and 28.5%, overall yield, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.