allyl 6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside | 110319-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-prop-2-enoxyoxane-3,4,5-triol
• CAS: 110319-36-3
• 化学式: C₂₅H₃₄O₆Si
• 分子量: 458.627
• InChiKey: IDSPEJNJMQTLCE-OYTPZHDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	allyl 6-O-(tert-butyldiphenylsilyl)-2,3,4-tris-O-(p-phenylbenzoyl)-β-D-galactopyranoside	110319-41-0	C64H58O9Si	999.245

反应信息

• 作为反应物：
  描述：

  allyl 6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 在 2,4,6-三甲基吡啶 、 甲醇 、 4-二甲氨基吡啶 、 乙酰氯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 allyl 2,3,4-tris-O-(phenylbenzoyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Selective silylation of .beta.-D-galactosides. A new approach to the synthesis of (1 .fwdarw. 6)-.beta.-D-galactopyranooligosaccharides

  摘要：

  DOI：

  10.1021/jo00232a036
• 作为产物：
  描述：

  allyl β-D-galactopyranoside 、 叔丁基二苯基氯硅烷 在 吡啶 作用下， 反应 4.0h， 生成 allyl 6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Rapid Oligosaccharide Synthesis Using a Fluorous Protective Group

  摘要：

  The Bfp-OH, a novel fluorous protecting reagent, was able to be easily prepared. The Bfp group was readily introduced to a carbohydrate, removed in high yield, and recyclable after cleavage. The use of the Bfp group made it possible to synthesize a pentasaccharide by minimal column chromatography purification. Each synthetic intermediate was able to be easily purified only by simple fluorous-organic solvent extraction and monitored by TLC, NMR, and MS.

  DOI：

  10.1021/jo049425k

文献信息

• Rapid Oligosaccharide Synthesis Using a Fluorous Protective Group
  作者：Tsuyoshi Miura、Kohtaro Goto、Hideki Waragai、Hiroharu Matsumoto、Yuriko Hirose、Masashi Ohmae、Hide-ki Ishida、Ai Satoh、Toshiyuki Inazu

  DOI：10.1021/jo049425k

  日期：2004.8.1

  The Bfp-OH, a novel fluorous protecting reagent, was able to be easily prepared. The Bfp group was readily introduced to a carbohydrate, removed in high yield, and recyclable after cleavage. The use of the Bfp group made it possible to synthesize a pentasaccharide by minimal column chromatography purification. Each synthetic intermediate was able to be easily purified only by simple fluorous-organic solvent extraction and monitored by TLC, NMR, and MS.
• Selective silylation of .beta.-D-galactosides. A new approach to the synthesis of (1 .fwdarw. 6)-.beta.-D-galactopyranooligosaccharides
  作者：Eugenia M. Nashed、Cornelis P. J. Glaudemans

  DOI：10.1021/jo00232a036

  日期：1987.11