1,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 1038507-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-2-[(2S,3S,4R,5R)-4-phenylmethoxy-2,5-bis(phenylmethoxymethyl)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxolan-3-yl]oxy-6-(phenylmethoxymethyl)oxane
• CAS: 1038507-74-2
• 化学式: C₉₅H₉₈O₁₆
• 分子量: 1495.81
• InChiKey: SETLBHYCENYNMY-FWYMQCCXSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  111
• 可旋转键数：
  41
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  三乙基硅烷 、 1,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-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 18.25h， 以85%的产率得到1,4-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-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
• 作为产物：
  描述：

  溴甲苯 、 D-(+)-松三糖水合物 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到1,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  在酸性条件下，通过在完全苄基化的蔗糖和蔗糖相关寡糖中β-果糖呋喃糖苷键的选择性裂解，制备部分苄基化的单糖，二糖和三糖

  摘要：

  通过选择性地在完全苄基化的蔗糖和衍生自乳糖蔗糖，棉子糖，松三糖，水苏糖和核糖的蔗糖相关的低聚糖中，β-果糖呋喃糖苷键的选择性裂解，成功制备了具有异头羟基的部分部分苄基化的单糖，二糖和三糖在酸性条件下，使用1:10 75％硫酸-二恶烷水溶液在室温下放置1h。

  DOI：

  10.1016/j.carres.2008.03.024

文献信息

• 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%).
• Preparation of partially benzylated mono-, di-, and trisaccharides by selective cleavage of the β-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides under acidic conditions
  作者：Takashi Yamanoi、Noriko Misawa、Sho Matsuda、Mikio Watanabe

  DOI：10.1016/j.carres.2008.03.024

  日期：2008.6

  Several partially benzylated mono-, di-, and trisaccharides having an anomeric hydroxyl group were successfully prepared by selective cleavage of the beta-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides derived from lactosucrose, raffinose, melezitose, stachyose, and nystose under acidic conditions using 1:10 75% aqueous sulfuric acid-dioxane at room temperature

  通过选择性地在完全苄基化的蔗糖和衍生自乳糖蔗糖，棉子糖，松三糖，水苏糖和核糖的蔗糖相关的低聚糖中，β-果糖呋喃糖苷键的选择性裂解，成功制备了具有异头羟基的部分部分苄基化的单糖，二糖和三糖在酸性条件下，使用1:10 75％硫酸-二恶烷水溶液在室温下放置1h。