1-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidene-10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-L-galacto-decitol | 408496-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidene-10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-L-galacto-decitol
• 英文别名: methyl 6-[(4S,5R)-5-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]hexanoate
• CAS: 408496-83-3
• 化学式: C₂₄H₄₆O₇Si
• 分子量: 474.711
• InChiKey: XYKGSGNYGCISKV-ZSXPUABSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidene-10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-L-galacto-decitol 在 四丁基氟化铵 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以17.7 g的产率得到2,3;4,5-di-O-isopropylidene-10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-L-galacto-decitol
  参考文献：
  名称：

  SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUES1

  摘要：

  Starting from 6-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidenealdehydo-D-galactose (1), the carbon backbone elongated GDP-L-fucose analogue 15 bearing a chromophore tag at the end of a spacer was synthesized. Additionally, the analogues of 3-L-fucosyllactose (29) and 2'-L-fucosyllactose (36), where the fucosyl moiety is marked by a five atom alkyl chain at C-5, were prepared as labeled oligosaccharides of human milk.

  DOI：

  10.1081/car-100108277
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 在 palladium on activated charcoal 四丁基溴化铵 、 氢气 、 碳酸氢钠 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正庚烷 、 氯仿 为溶剂， 反应 48.75h， 生成 1-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidene-10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-L-galacto-decitol
  参考文献：
  名称：

  SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUES1

  摘要：

  Starting from 6-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidenealdehydo-D-galactose (1), the carbon backbone elongated GDP-L-fucose analogue 15 bearing a chromophore tag at the end of a spacer was synthesized. Additionally, the analogues of 3-L-fucosyllactose (29) and 2'-L-fucosyllactose (36), where the fucosyl moiety is marked by a five atom alkyl chain at C-5, were prepared as labeled oligosaccharides of human milk.

  DOI：

  10.1081/car-100108277

文献信息

• SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUES1
  作者：Andrej-Jakob Ott、Meinolf Brackhagen、Anahit Davtyan、Birte Nolting、Hanna Boye、Astrid Schoknecht、Christian Vogel

  DOI：10.1081/car-100108277

  日期：——

  Starting from 6-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidenealdehydo-D-galactose (1), the carbon backbone elongated GDP-L-fucose analogue 15 bearing a chromophore tag at the end of a spacer was synthesized. Additionally, the analogues of 3-L-fucosyllactose (29) and 2'-L-fucosyllactose (36), where the fucosyl moiety is marked by a five atom alkyl chain at C-5, were prepared as labeled oligosaccharides of human milk.