methyl 2-acetamido-2,6-dideoxy-6-iodo-β-D-allopyranoside | 1198410-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2,6-dideoxy-6-iodo-β-D-allopyranoside
• 英文别名: N-[(2R,3R,4S,5S,6S)-4,5-dihydroxy-6-(iodomethyl)-2-methoxyoxan-3-yl]acetamide
• CAS: 1198410-08-0
• 化学式: C₉H₁₆INO₅
• 分子量: 345.134
• InChiKey: UDWIKJFZBKKCBS-GOFVFXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-2,6-dideoxy-6-iodo-β-D-allopyranoside 在 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 N-[(3R,4S,5R)-5-ethenyl-2,4-dihydroxyoxolan-3-yl]acetamide
  参考文献：
  名称：

  Efficient synthesis of d-xylo and d-ribo-phytosphingosines from methyl 2-amino-2-deoxy-β-d-hexopyranosides

  摘要：

  A general and flexible synthetic approach to biologically important 5,6-unsaturated C-18-phytosphingosines was developed via olefin cross-metathesis employing truncated C-6-phytosphingosines as the key intermediates. These were efficiently prepared in high yields by zinc-mediated reductive opening of methyl 2-amino-2-deoxy-beta-hexopyranosides.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.07.007
• 作为产物：
  描述：

  methyl N-acetyl-β-D-glucosamine 在 吡啶 、 四碘甲烷 、 三苯基膦 作用下， 反应 6.0h， 以71%的产率得到methyl 2-acetamido-2,6-dideoxy-6-iodo-β-D-allopyranoside
  参考文献：
  名称：

  Efficient synthesis of d-xylo and d-ribo-phytosphingosines from methyl 2-amino-2-deoxy-β-d-hexopyranosides

  摘要：

  A general and flexible synthetic approach to biologically important 5,6-unsaturated C-18-phytosphingosines was developed via olefin cross-metathesis employing truncated C-6-phytosphingosines as the key intermediates. These were efficiently prepared in high yields by zinc-mediated reductive opening of methyl 2-amino-2-deoxy-beta-hexopyranosides.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.07.007

文献信息

• Efficient synthesis of d-xylo and d-ribo-phytosphingosines from methyl 2-amino-2-deoxy-β-d-hexopyranosides
  作者：Ye Cai、Chang-Chun Ling、David R. Bundle

  DOI：10.1016/j.carres.2009.07.007

  日期：2009.11

  A general and flexible synthetic approach to biologically important 5,6-unsaturated C-18-phytosphingosines was developed via olefin cross-metathesis employing truncated C-6-phytosphingosines as the key intermediates. These were efficiently prepared in high yields by zinc-mediated reductive opening of methyl 2-amino-2-deoxy-beta-hexopyranosides.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.