methyl 6-O-(2’-acetamido-3’,4’,6’-tri-O-benzyl-2’-deoxy-α-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-(2’-acetamido-3’,4’,6’-tri-O-benzyl-2’-deoxy-α-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: Bn(-3)[Bn(-4)][Bn(-6)]GlcNAc(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Glc1Me；N-[(2S,3R,4R,5S,6R)-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• 化学式: C₅₇H₆₃NO₁₁
• 分子量: 938.127
• InChiKey: AUBFKDAGEOJLRO-CGHFQLQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  69
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-Acetamido-1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranose 、 甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 在 三氟化硼乙醚 、 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以45.7 mg的产率得到methyl O-(2-N-acetylamino-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Formation of 2-Acetamido-2-deoxy-D-glucopyranosidic Linkages via Glycosidation Using a Combination of Two Lewis Acids

  摘要：

  A mixed activation system composed of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promotes the glycosylation of various alcohol acceptors using 2-acetamido-3,4,6-tri-O-benzy1-2-deoxy-alpha-D-glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-D-glucopyranosides in good yields with significant formation of the alpha-isomers. Notably, stereoselective glycosylations of phenol derivatives as the acceptors afforded aryl 1,2-cis-alpha-glycosides without the formation of any beta-isomers. This highly stereocontrolled 1,2-cis-alpha-glycosidation was applied to the synthesis of a novel hydroquinone alpha-glycoside.

  DOI：

  10.3987/com-14-s(k)4

文献信息

• Formation of 2-Acetamido-2-deoxy-D-glucopyranosidic Linkages via Glycosidation Using a Combination of Two Lewis Acids
  作者：Takashi Yamanoi、Yoshiki Oda、Masanobu Midorikawa

  DOI：10.3987/com-14-s(k)4

  日期：——

  A mixed activation system composed of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promotes the glycosylation of various alcohol acceptors using 2-acetamido-3,4,6-tri-O-benzy1-2-deoxy-alpha-D-glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-D-glucopyranosides in good yields with significant formation of the alpha-isomers. Notably, stereoselective glycosylations of phenol derivatives as the acceptors afforded aryl 1,2-cis-alpha-glycosides without the formation of any beta-isomers. This highly stereocontrolled 1,2-cis-alpha-glycosidation was applied to the synthesis of a novel hydroquinone alpha-glycoside.