4-O-methylphenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-methylphenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: Bn(-3)[Bn(-4)][Bn(-6)]GlcNAc(a)-O-Ph(4-OMe)；N-[(2R,3R,4R,5S,6R)-2-(4-methoxyphenoxy)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• 化学式: C₃₆H₃₉NO₇
• 分子量: 597.708
• InChiKey: DXDYJVLOFUIGIR-HFDGEQGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  7

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 、 4-甲氧基苯酚 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84%的产率得到4-O-methylphenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-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 1,2-cis-α-Aryl-glycosidic Linkages Directly from 2-Acetamido-2-deoxy-D-glucopyranosyl Acetate by the Mixed Activating System Using Ytterbium(III) Triflate and Catalytic Boron Trifluoride Diethyl Etherate Complex
  作者：Takashi Yamanoi、Masanobu Midorikawa、Yoshiki Oda

  DOI：10.3987/com-13-s(s)44

  日期：——

  We found that a mixed activating system using ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promoted glycosidation of the 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-alpha-D-glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-D-glucopyranosides in good yields along with the formation of a considerable amount of alpha-isomers. Glycosylations of the aryl alcohols as the acceptors stereoselectively afforded aryl alpha-glycosides without producing any beta-isomers.
• 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.