1-O-tert-butyldiphenylsilyl-3,4,6-tri-O-benzoyl-β-D-fructofuranosyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside | 309261-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-tert-butyldiphenylsilyl-3,4,6-tri-O-benzoyl-β-D-fructofuranosyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
• 英文别名: 1'-O-tert-butyldiphenylsilyl-2,3,4,6,3',4',6'-hepta-O-benzoylsucrose；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 309261-82-3
• 化学式: C₇₇H₆₈O₁₈Si
• 分子量: 1309.46
• InChiKey: HIQGHLMLWXDCJW-YEWWXFSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.24
• 重原子数：
  96
• 可旋转键数：
  31
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyldiphenylsilyl-3,4,6-tri-O-benzoyl-β-D-fructofuranosyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.0h， 生成 1-O-acetyl-3,4,6-tri-O-benzoyl-β-D-fructofuranosyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Preparation of sucrose heptaesters unsubstituted at the C-1 hydroxy group of the fructose moiety via selective O-desilylation

  摘要：

  Selective O-desilylation of 6,1',6-tri-O-tert-butyldiphenylsilyl-2,3,4,3',4'-penta-O-benzoylsucrose with hydrofluoric acid in acetonitrile led to the 1'-O-tert-butyldiphenylsilyl derivative (96% yield), which was further perbenzoylated and deprotected at OH-1' with tetrabutylammonium fluoride (86%). An analogous sequence with the corresponding O-acetylated sucrose derivative and tetrabutylammonium fluoride as desilylating agent resulted in a lower yield of the C-1' hydroxy derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00119-1
• 作为产物：
  描述：

  苯甲酰氯 、 1-O-tert-butyldiphenylsilyl-3,4-di-O-benzoyl-β-D-fructofuranosyl-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 以100%的产率得到1-O-tert-butyldiphenylsilyl-3,4,6-tri-O-benzoyl-β-D-fructofuranosyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Preparation of sucrose heptaesters unsubstituted at the C-1 hydroxy group of the fructose moiety via selective O-desilylation

  摘要：

  Selective O-desilylation of 6,1',6-tri-O-tert-butyldiphenylsilyl-2,3,4,3',4'-penta-O-benzoylsucrose with hydrofluoric acid in acetonitrile led to the 1'-O-tert-butyldiphenylsilyl derivative (96% yield), which was further perbenzoylated and deprotected at OH-1' with tetrabutylammonium fluoride (86%). An analogous sequence with the corresponding O-acetylated sucrose derivative and tetrabutylammonium fluoride as desilylating agent resulted in a lower yield of the C-1' hydroxy derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00119-1

文献信息

• Chemical Synthesis of 1′-Deoxy-1′-fluorosucrose
  作者：Weijiang Ying、Vikram Gaddam、Michael Harmata

  DOI：10.1021/ol401044h

  日期：2013.6.7

  The first chemical synthesis of 1'-deoxy-1'-fluorosucrose has been accomplished in eight steps from sucrose by an unlikely, but ultimately successful, S(N)2 displacement reaction.
• Preparation of sucrose heptaesters unsubstituted at the C-1 hydroxy group of the fructose moiety via selective O-desilylation
  作者：M.Teresa Barros、Christopher D. Maycock、Christine Thomassigny

  DOI：10.1016/s0008-6215(00)00119-1

  日期：2000.9

  Selective O-desilylation of 6,1',6-tri-O-tert-butyldiphenylsilyl-2,3,4,3',4'-penta-O-benzoylsucrose with hydrofluoric acid in acetonitrile led to the 1'-O-tert-butyldiphenylsilyl derivative (96% yield), which was further perbenzoylated and deprotected at OH-1' with tetrabutylammonium fluoride (86%). An analogous sequence with the corresponding O-acetylated sucrose derivative and tetrabutylammonium fluoride as desilylating agent resulted in a lower yield of the C-1' hydroxy derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.