6-amino-6-deoxy-6-C-hydroxymethyl-1,2-O-isopropylidene-α-D-gluco-heptofuranose | 1107060-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-amino-6-deoxy-6-C-hydroxymethyl-1,2-O-isopropylidene-α-D-gluco-heptofuranose
• 英文别名: (1R)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-amino-2-(hydroxymethyl)propane-1,3-diol
• CAS: 1107060-47-8
• 化学式: C₁₁H₂₁NO₇
• 分子量: 279.29
• InChiKey: KUBLKTKUDGIKCZ-VRGHQRLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-amino-6-deoxy-6-C-hydroxymethyl-1,2-O-isopropylidene-α-D-gluco-heptofuranose 在 水 、 三氟乙酸 作用下， 反应 4.0h， 生成 6-amino-6-deoxy-6-C-hydroxymethyl-α-D-gluco-heptofuranose 、 6-amino-6-deoxy-6-C-hydroxymethyl-β-D-gluco-heptofuranose
  参考文献：
  名称：

  Studies on the transformation of nitrosugars into branched chain iminosugars. Part II: Synthesis of (3R,4R,5R,6S)-2,2-bis(hydroxymethyl)azepane-3,4,5,6-tetraol

  摘要：

  The first stereocontrolled synthesis of (3R,4R,5R,6S)-2,2-bis-(hydroxymethyi)azepane-3,4,5,6-tetraol is described herein. The method involves a novel double Henry reaction of the 3,5-di-O-benzyl-6-deoxy-1,2 -O-isopropyIidene-6-nitro-alpha-D-glucofuranose with formaldehyde followed by a reductive ring closure to give the first branched 1,6-dideoxy-1,6-heptitol described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.027
• 作为产物：
  描述：

  3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-nitro-α-D-glucofuranose 在 甲酸铵 、 钯 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 6-amino-6-deoxy-6-C-hydroxymethyl-1,2-O-isopropylidene-α-D-gluco-heptofuranose
  参考文献：
  名称：

  Studies on the transformation of nitrosugars into branched chain iminosugars. Part II: Synthesis of (3R,4R,5R,6S)-2,2-bis(hydroxymethyl)azepane-3,4,5,6-tetraol

  摘要：

  The first stereocontrolled synthesis of (3R,4R,5R,6S)-2,2-bis-(hydroxymethyi)azepane-3,4,5,6-tetraol is described herein. The method involves a novel double Henry reaction of the 3,5-di-O-benzyl-6-deoxy-1,2 -O-isopropyIidene-6-nitro-alpha-D-glucofuranose with formaldehyde followed by a reductive ring closure to give the first branched 1,6-dideoxy-1,6-heptitol described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.027

文献信息

• Studies on the transformation of nitrosugars into branched chain iminosugars. Part II: Synthesis of (3R,4R,5R,6S)-2,2-bis(hydroxymethyl)azepane-3,4,5,6-tetraol
  作者：José M. Otero、Amalia M. Estévez、Raquel G. Soengas、Juan C. Estévez、Robert J. Nash、George W.J. Fleet、Ramón J. Estévez

  DOI：10.1016/j.tetasy.2008.10.027

  日期：2008.11

  The first stereocontrolled synthesis of (3R,4R,5R,6S)-2,2-bis-(hydroxymethyi)azepane-3,4,5,6-tetraol is described herein. The method involves a novel double Henry reaction of the 3,5-di-O-benzyl-6-deoxy-1,2 -O-isopropyIidene-6-nitro-alpha-D-glucofuranose with formaldehyde followed by a reductive ring closure to give the first branched 1,6-dideoxy-1,6-heptitol described. (C) 2008 Elsevier Ltd. All rights reserved.