6,1',6'-tri-O-tert-butyldiphenylsilyl-2,3,4,6,3',4'-penta-O-benzoylsucrose | 81087-01-6

• 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: 6,1',6'-tri-O-tert-butyldiphenylsilyl-2,3,4,6,3',4'-penta-O-benzoylsucrose
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-2,5-bis[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]oxyoxan-3-yl] benzoate
• CAS: 81087-01-6
• 化学式: C₉₅H₉₆O₁₆Si₃
• 分子量: 1578.05
• InChiKey: FEVOWVGCKRORBA-XICIYYPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.68
• 重原子数：
  114
• 可旋转键数：
  35
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  187
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  6,1',6'-tri-O-tert-butyldiphenylsilyl-2,3,4,6,3',4'-penta-O-benzoylsucrose 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以96%的产率得到1-O-tert-butyldiphenylsilyl-3,4-di-O-benzoyl-β-D-fructofuranosyl-2,3,4-tri-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 、 6,1',6'-tri-O-tert-butyldiphenylsilyl sucrose 在 吡啶 作用下， 反应 2.0h， 以94%的产率得到6,1',6'-tri-O-tert-butyldiphenylsilyl-2,3,4,6,3',4'-penta-O-benzoylsucrose
  参考文献：
  名称：

  Chemical Synthesis of 1′-Deoxy-1′-fluorosucrose

  摘要：

  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.

  DOI：

  10.1021/ol401044h

文献信息

• Synthesis and reactions of tert-butyldiphenylsilyl ethers of sucrose
  作者：Horst Karl、Cheang Kuan Lee、Riaz Khan

  DOI：10.1016/s0008-6215(00)80792-2

  日期：1982.2

  Abstract The reaction of sucrose with 1.1 mol. equiv. of tert-butyldiphenylsilyl (t-BDPS) chloride in pyridine in the presence of 4-dimethylaminopyridine gave the crystalline 6′-t-BDPS ether 1 in 49% yield, without recourse to column chromatography. Compound 1 was transformed into the 4,6,1′-trichloride by using sulphuryl chloride. When the silylation reaction of sucrose was performed with 3 mol. equiv

  摘要蔗糖与1.1 mol的蔗糖反应。当量 在4-二甲基氨基吡啶存在下，在吡啶中氯化叔丁基二苯基甲硅烷基（t-BDPS）产生结晶的6'-t-BDPS醚1，无需借助柱色谱法。通过使用磺酰氯将化合物1转化为4,6,1'-三氯化物。当用3摩尔蔗糖进行甲硅烷基化反应时。当量 对该试剂进行色谱纯化，得到结晶的6,6'-二-t-BDPS醚和6,1'，6'-三-t-BDPS醚9，产率分别为78和18.7％。获得化合物9作为用4.6mol蔗糖处理的主要产物。当量 甲硅烷基化试剂。使用氟化四丁基铵顺利地除去6,6'-二-O-叔丁基-二苯基甲硅烷基蔗糖六苯甲酸酯中的甲硅烷基保护基
• 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.
• 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.