2,3,3',4,6-penta-O-benzyl-6'-O-tert-butyldimethylsilyl-1',4'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)sucrose | 302905-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,3',4,6-penta-O-benzyl-6'-O-tert-butyldimethylsilyl-1',4'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)sucrose
• 英文别名: tert-butyl-dimethyl-[[(1R,8S,10R,11S)-11-phenylmethoxy-3,3,5,5-tetra(propan-2-yl)-8-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2,4,6,9-tetraoxa-3,5-disilabicyclo[6.2.1]undecan-10-yl]methoxy]silane
• CAS: 302905-27-7
• 化学式: C₆₅H₉₂O₁₂Si₃
• 分子量: 1149.69
• InChiKey: ASOWUENYFLXKSO-OSROZRSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.36
• 重原子数：
  80
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,3',4,6-penta-O-benzyl-6'-O-tert-butyldimethylsilyl-1',4'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)sucrose 在 tris(dimethylamino)sulfonium trimethylsilyldifluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以100%的产率得到2,3,3',4,6-penta-O-benzylsucrose
  参考文献：
  名称：

  A Novel β-Directing Fructofuranosyl Donor Concept. Stereospecific Synthesis of Sucrose

  摘要：

  A new concept for the construction of beta-D-fructofuranosides based on the idea of locking the anomeric CH2OH group to the alpha-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycoside fructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridge have been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) as promoter. The couplings were stereospecific to give beta-D-fructofuranosyl disaccharides in high yields. Using this approach, sucrose has been synthesized stereospecifically in 80% yield.

  DOI：

  10.1021/ja001439u
• 作为产物：
  描述：

  ethyl 2-thio-β-D-fructofuranoside 在 吡啶 、 咪唑 、 三乙基硅烷 、 4-二甲氨基吡啶 、 sodium hydroxide 、 di-tert-butylmethylpyridine 、 四丁基硫酸氢铵 、 DMTST 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 131.0h， 生成 2,3,3',4,6-penta-O-benzyl-6'-O-tert-butyldimethylsilyl-1',4'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)sucrose
  参考文献：
  名称：

  A Novel β-Directing Fructofuranosyl Donor Concept. Stereospecific Synthesis of Sucrose

  摘要：

  A new concept for the construction of beta-D-fructofuranosides based on the idea of locking the anomeric CH2OH group to the alpha-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycoside fructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridge have been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) as promoter. The couplings were stereospecific to give beta-D-fructofuranosyl disaccharides in high yields. Using this approach, sucrose has been synthesized stereospecifically in 80% yield.

  DOI：

  10.1021/ja001439u

文献信息

• A Novel β-Directing Fructofuranosyl Donor Concept. Stereospecific Synthesis of Sucrose
  作者：Stefan Oscarson、Fernando W. Sehgelmeble

  DOI：10.1021/ja001439u

  日期：2000.9.1

  A new concept for the construction of beta-D-fructofuranosides based on the idea of locking the anomeric CH2OH group to the alpha-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycoside fructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridge have been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) as promoter. The couplings were stereospecific to give beta-D-fructofuranosyl disaccharides in high yields. Using this approach, sucrose has been synthesized stereospecifically in 80% yield.