1,2,3-trideoxy-5,6;8,9-di-O-isopropylidene-D-manno-non-1-yno-4-ulofuranose | 1346258-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3-trideoxy-5,6;8,9-di-O-isopropylidene-D-manno-non-1-yno-4-ulofuranose
• 英文别名: (3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-prop-2-ynyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ol
• CAS: 1346258-05-6
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: VWSJFVKKECEVHZ-KLFGWDPYSA-N

物化性质

• 沸点：
  393.1±42.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2,3-trideoxy-5,6;8,9-di-O-isopropylidene-D-manno-non-1-yno-4-ulofuranose 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 臭氧 、 silver nitrate 、 溶剂黄146 作用下， 以 甲醇 、 二甲基硫 、 水 、 丙酮 为溶剂， 反应 65.0h， 生成 3-脱氧-D-甘油-D-乳-2-吡喃壬酮糖酸
  参考文献：
  名称：

  Practical Synthesis of 2-Keto-3-deoxy-d-glycero-d-galactononulosonic Acid (KDN)

  摘要：

  Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-Isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the alpha-keto acid moiety from the alkyne.

  DOI：

  10.1021/ol202773t
• 作为产物：
  描述：

  allenylmagnesium bromide 、 2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 以 四氢呋喃 、 甲苯 为溶剂， 生成 1,2,3-trideoxy-5,6;8,9-di-O-isopropylidene-D-manno-non-1-yno-4-ulofuranose
  参考文献：
  名称：

  Practical Synthesis of 2-Keto-3-deoxy-d-glycero-d-galactononulosonic Acid (KDN)

  摘要：

  Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-Isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the alpha-keto acid moiety from the alkyne.

  DOI：

  10.1021/ol202773t

文献信息

• Practical Synthesis of 2-Keto-3-deoxy-<scp>d</scp>-glycero-<scp>d</scp>-galactononulosonic Acid (KDN)
  作者：David Crich、Chandrasekhar Navuluri

  DOI：10.1021/ol202773t

  日期：2011.12.2

  Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-Isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the alpha-keto acid moiety from the alkyne.