methyl [3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-fructofuranosyl]-(1->6)-2,3,4-tri-O-benzyl-αD-mannopyranoside | 302905-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-fructofuranosyl]-(1->6)-2,3,4-tri-O-benzyl-αD-mannopyranoside
• 英文别名: tert-butyl-[[(1R,8R,10R,11S)-8-[[(2R,3R,4S,5S,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-11-phenylmethoxy-3,3,5,5-tetra(propan-2-yl)-2,4,6,9-tetraoxa-3,5-disilabicyclo[6.2.1]undecan-10-yl]methoxy]-diphenylsilane
• CAS: 302905-24-4
• 化学式: C₆₉H₉₂O₁₂Si₃
• 分子量: 1197.74
• InChiKey: IOIXGORTNHRVET-GNIUNWMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.34
• 重原子数：
  84
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  methyl [3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-fructofuranosyl]-(1->6)-2,3,4-tri-O-benzyl-αD-mannopyranoside 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methyl [3-O-benzyl-β-D-fructofuranosyl]-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  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 methyl [3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-fructofuranosyl]-(1->6)-2,3,4-tri-O-benzyl-αD-mannopyranoside
  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.