1-bromo-4,7-di-O-[(t-butyl)dimethylsilyl]-1,2,3-trideoxy-5,6:8,9-di-O-isopropylidene-D-glycero-D-galacto-1-yno-nonitol | 1346258-16-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-4,7-di-O-[(t-butyl)dimethylsilyl]-1,2,3-trideoxy-5,6:8,9-di-O-isopropylidene-D-glycero-D-galacto-1-yno-nonitol
• 英文别名: [(R)-[(4R,5S)-5-[(1S)-4-bromo-1-[tert-butyl(dimethyl)silyl]oxybut-3-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-tert-butyl-dimethylsilane
• CAS: 1346258-16-9
• 化学式: C₂₇H₅₁BrO₆Si₂
• 分子量: 607.773
• InChiKey: DYPQUWJVGDSDQU-VJFDXUIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-bromo-4,7-di-O-[(t-butyl)dimethylsilyl]-1,2,3-trideoxy-5,6:8,9-di-O-isopropylidene-D-glycero-D-galacto-1-yno-nonitol 在 臭氧 、 二甲基硫 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 28.0h， 以33%的产率得到methyl 3,6-di-O-[(t-butyl)dimethylsilyl]-2-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanoate
  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：

  2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 80.0h， 生成 1-bromo-4,7-di-O-[(t-butyl)dimethylsilyl]-1,2,3-trideoxy-5,6:8,9-di-O-isopropylidene-D-glycero-D-galacto-1-yno-nonitol
  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.