benzyl (3,4-di-O-benzoyl-2-O-methyl-α-L-fucopyranosyl)-(1-6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 181875-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (3,4-di-O-benzoyl-2-O-methyl-α-L-fucopyranosyl)-(1-6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-4-benzoyloxy-6-[[(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-3-hydroxy-4,6-bis(phenylmethoxy)oxan-2-yl]methoxy]-5-methoxy-2-methyloxan-3-yl] benzoate
• CAS: 181875-91-2
• 化学式: C₄₉H₄₇NO₁₃
• 分子量: 857.911
• InChiKey: UFKMNKBTYZRRMX-KEFRHYDYSA-N

物化性质

• 沸点：
  921.346±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.384±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  63
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  166
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  benzyl (3,4-di-O-benzoyl-2-O-methyl-α-L-fucopyranosyl)-(1-6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到
  参考文献：
  名称：

  使用氯化铁对复杂寡糖进行脱苄基作用

  摘要：

  室温和0°C下的CH 2 Cl 2中的无水FeCl 3已用于脱除单糖和寡糖的苄基，收率通常大于70％。值得注意的是，烯烃，乙酸酯，苯甲酸酯，邻苯二甲酰亚胺，酰基酰胺和敏感的糖苷键不受反应条件的影响。

  DOI：

  10.1016/0040-4039(96)01169-0
• 作为产物：
  描述：

  2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 在 盐酸 、 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 46.59h， 生成 benzyl (3,4-di-O-benzoyl-2-O-methyl-α-L-fucopyranosyl)-(1-6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  TCP- and Phthalimide-Protected n-Pentenyl Glucosaminide Precursors for the Synthesis of Nodulation Factors As Illustrated by the Total Synthesis of NodRf-III (C18:1, MeFuc)

  摘要：

  TCP- and phthalimide-protected n-pentenyl glucosaminide (NPG) precursors have been utilized in a convergent stereocontrolled synthesis of the nodulation factor NodRf-III (C18:1, MeFuc) produced by Rhizobium fredii USDA257, 2. Nodulation factors are lipooligosaccharides that are secreted by bacteria which trigger the early steps in the formation of root nodules in leguminous plants. This symbiotic relationship between plant and bacteria plays a major role in the global nitrogen cycle. Key to our synthetic approach was the use of the TCP (tetrachlorophthaloyl) group to provide for N-differentiation of the linear glucosamine backbone and the use of FeCl3 for the removal of benzyl protecting groups from the tetrasaccharide. The saccharide skeleton was assembled via the NPG-based coupling of a linear beta(1-->4) glucosamine disaccharide to a 6-O-fucosylated glucosamine acceptor. Significant yield enhancements for NPG couplings were observed at lower temperatures. Subsequent exchange of benzyl to tert-butyldimethylsilyl protecting groups via FeCl3 mediation and installation of the fatty chain on the nonreducing terminus via selective removal of TCP led to a late intermediate which was deprotected in high yield to afford the natural product.

  DOI：

  10.1021/jo962362o

文献信息

• Nodulation Factors:  A Strategy for Convergent Assembly of a Late-Stage Key Intermediate Illustrated by the Total Synthesis of NodRf-III (C18:1) (MeFuc)
  作者：John S. Debenham、Robert Rodebaugh、Bert Fraser-Reid

  DOI：10.1021/jo961115h

  日期：1996.1.1
• Debenzylation of complex oligosaccharides using ferric chloride
  作者：Robert Rodebaugh、John S Debenham、Bert Fraser-Reid

  DOI：10.1016/0040-4039(96)01169-0

  日期：1996.7

  Anhydrous FeCl3 in CH2Cl2 at room temperature and 0 °C has been used to debenzylate monosaccharides and oligosaccharides in yields generally greater than 70%. Notably, alkenes, acetates, benzoates, phthalimides, acyl amides, and sensitive glycosidic linkages are unaffected by the reaction conditions.

  室温和0°C下的CH 2 Cl 2中的无水FeCl 3已用于脱除单糖和寡糖的苄基，收率通常大于70％。值得注意的是，烯烃，乙酸酯，苯甲酸酯，邻苯二甲酰亚胺，酰基酰胺和敏感的糖苷键不受反应条件的影响。
• TCP- and Phthalimide-Protected <i>n</i>-Pentenyl Glucosaminide Precursors for the Synthesis of Nodulation Factors As Illustrated by the Total Synthesis of NodRf-III (C18:1, MeFuc)
  作者：John S. Debenham、Robert Rodebaugh、Bert Fraser-Reid

  DOI：10.1021/jo962362o

  日期：1997.7.1

  TCP- and phthalimide-protected n-pentenyl glucosaminide (NPG) precursors have been utilized in a convergent stereocontrolled synthesis of the nodulation factor NodRf-III (C18:1, MeFuc) produced by Rhizobium fredii USDA257, 2. Nodulation factors are lipooligosaccharides that are secreted by bacteria which trigger the early steps in the formation of root nodules in leguminous plants. This symbiotic relationship between plant and bacteria plays a major role in the global nitrogen cycle. Key to our synthetic approach was the use of the TCP (tetrachlorophthaloyl) group to provide for N-differentiation of the linear glucosamine backbone and the use of FeCl3 for the removal of benzyl protecting groups from the tetrasaccharide. The saccharide skeleton was assembled via the NPG-based coupling of a linear beta(1-->4) glucosamine disaccharide to a 6-O-fucosylated glucosamine acceptor. Significant yield enhancements for NPG couplings were observed at lower temperatures. Subsequent exchange of benzyl to tert-butyldimethylsilyl protecting groups via FeCl3 mediation and installation of the fatty chain on the nonreducing terminus via selective removal of TCP led to a late intermediate which was deprotected in high yield to afford the natural product.