1,3,4-tri-O-benzyl-6-O-triethyl-silyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 1206803-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4-tri-O-benzyl-6-O-triethyl-silyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: 1,3,4-tri-O-benzyl-6-O-triethylsilyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside；[(2R,3R,4S,5S)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxolan-2-yl]methoxy-triethylsilane
• CAS: 1206803-49-7
• 化学式: C₆₇H₇₈O₁₁Si
• 分子量: 1087.44
• InChiKey: NZMMQTOAMDMGSX-MNJFILODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.21
• 重原子数：
  79
• 可旋转键数：
  31
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,3,4-tri-O-benzyl-6-O-triethyl-silyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1,3,4-tri-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Co 2（CO）8 / Et 3 SiH / CO系统的区域选择性脱-O-苄化反应合成棉子糖家族寡糖

  摘要：

  提出了一种方便的方法，以蔗糖为原料合成棉子糖，水苏糖和马齿c糖。关键步骤是使用Co 2（CO）8 / Et 3 SiH / CO系统进行区域选择性脱O-苄基化，然后进行高水平的α-选择性糖基化。新开发的脱-O-苄基化系统可在温和条件下以高选择性高效去除蔗糖和棉子糖的伯苄基。使用硫代糖苷作为供体，NIS / AgOTf作为启动子，DTBMP作为添加剂，酸不稳定蔗糖底物的糖基化可以实现高收率。

  DOI：

  10.1016/j.tet.2013.03.094
• 作为产物：
  描述：

  三乙基硅烷 、 1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 dicobalt octacarbonyl 、 一氧化碳 作用下， 以 苯 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 24.25h， 以85%的产率得到1,3,4-tri-O-benzyl-6-O-triethyl-silyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Highly Efficient and Mild Method for Regioselective De-O-benzylation of Saccharides by Co₂(CO)₈-Et₃SiH−CO Reagent System

  摘要：

  A highly efficient and mild method for the de-O-benzylation of protected saccharides was developed by transforming terminal benzyl ethers into silyl ethers using Co-2(CO)(8)-Et3SiH under 1 atm of CO. The method was successfully used for the de-O-benzylation of perbenzylated monosaccharides with various anomeric protecting groups, as well as natural disaccharides and trisaccharides such as sucrose, raffinose, and melezitose in good yields (>80%).

  DOI：

  10.1021/ol902717y

文献信息

• Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system
  作者：Yue-tao Zhao、Shan Niu、Lu-bai Huang、Ji-ming Wang、Zhao-jun Yin、Qing Li、Zhong-jun Li

  DOI：10.1016/j.tet.2013.03.094

  日期：2013.6

  key step is the regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system, followed by a high α-selective glycosylation. The newly developed de-O-benzylation system is efficient in removing the primary benzyl groups of sucrose and raffinose under mild condition and with high selectivity. Using thioglycoside as donor, NIS/AgOTf as promoter and DTBMP as additive, glycosylation of acid labile sucrose

  提出了一种方便的方法，以蔗糖为原料合成棉子糖，水苏糖和马齿c糖。关键步骤是使用Co 2（CO）8 / Et 3 SiH / CO系统进行区域选择性脱O-苄基化，然后进行高水平的α-选择性糖基化。新开发的脱-O-苄基化系统可在温和条件下以高选择性高效去除蔗糖和棉子糖的伯苄基。使用硫代糖苷作为供体，NIS / AgOTf作为启动子，DTBMP作为添加剂，酸不稳定蔗糖底物的糖基化可以实现高收率。
• Highly Efficient and Mild Method for Regioselective De-<i>O</i>-benzylation of Saccharides by Co₂(CO)₈-Et₃SiH−CO Reagent System
  作者：Zhao-Jun Yin、Bo Wang、Yang-Bing Li、Xiang-Bao Meng、Zhong-Jun Li

  DOI：10.1021/ol902717y

  日期：2010.2.5

  A highly efficient and mild method for the de-O-benzylation of protected saccharides was developed by transforming terminal benzyl ethers into silyl ethers using Co-2(CO)(8)-Et3SiH under 1 atm of CO. The method was successfully used for the de-O-benzylation of perbenzylated monosaccharides with various anomeric protecting groups, as well as natural disaccharides and trisaccharides such as sucrose, raffinose, and melezitose in good yields (>80%).