Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-allyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester | 749858-85-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-allyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester
• 英文别名: TBDPS(-6)Gal2Ac3Ac4Ac(b)-O-allyl；[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-prop-2-enoxyoxan-3-yl] acetate
• CAS: 749858-85-3
• 化学式: C₃₁H₄₀O₉Si
• 分子量: 584.739
• InChiKey: DHFFQRIDUUOTOC-HBMYTODVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-allyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 在 四(三苯基膦)钯 溶剂黄146 作用下， 反应 1.0h， 以80%的产率得到Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-tetrahydro-pyran-3-yl ester
  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
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 吡啶 作用下， 反应 23.0h， 生成 Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-allyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester
  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