Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2S,3R,4R,5S,6R)-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-6-hydroxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester | 212713-55-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2S,3R,4R,5S,6R)-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-6-hydroxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester
• CAS: 212713-55-8
• 化学式: C₃₄H₅₂Cl₃NO₁₃Si
• 分子量: 817.23
• InChiKey: FTATZKASAAQXIB-ICVXSRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  52.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  177.54
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2S,3R,4R,5S,6R)-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-6-hydroxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 192.42h， 生成 C₄₉H₅₆Cl₆N₂O₂₃
  参考文献：
  名称：

  Synthesis of Lewis a and Lewis X Pentasaccharides Based on N-Trichloroethoxycarbonyl Protection

  摘要：

  Thexyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-trichloroethoxycarbonylamino-beta-D-glucopyranoside (4), having the 3-hydroxy group unprotected, is a versatile starting material for the synthesis of glucosamine containing oligosaccharides. Thus, reaction with galactosyl donor 5 or fucosyl donor 6 afforded the desired beta(1-3)- and alpha(1-3)-linked disaccharides 7 and 8, respectively, in high yields, Reductive opening of the benzylidene moieties in 7 and 8 gave access to the 4-hydroxy groups in 9 and 10. Ensuing fucosylation of 9 or galactosylation of 10 led to Lewis A (Le(a)) and Lewis X (Le(x)) trisaccharide building blocks 13 and 14, respectively. Their transformation into glycosyl donors 19 and 20 and subsequent reaction with 3b-O-unprotected lactose derivative 23 as acceptor furnished the Le(a)- and Le(x) pentasaccharide precursors 24 and 25. Exchange of the N-trichloroethoxycarbonyl group for an N-acetyl group and removal of the O-benzyl and O-acetyl protective groups afforded the desired Le(a)- and Lex-pentasaccharides 1 and 2.

  DOI：

  10.1080/07328309808002349
• 作为产物：
  描述：

  C₄₁H₅₆Cl₃NO₁₃Si 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2S,3R,4R,5S,6R)-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-6-hydroxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of Lewis a and Lewis X Pentasaccharides Based on N-Trichloroethoxycarbonyl Protection

  摘要：

  Thexyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-trichloroethoxycarbonylamino-beta-D-glucopyranoside (4), having the 3-hydroxy group unprotected, is a versatile starting material for the synthesis of glucosamine containing oligosaccharides. Thus, reaction with galactosyl donor 5 or fucosyl donor 6 afforded the desired beta(1-3)- and alpha(1-3)-linked disaccharides 7 and 8, respectively, in high yields, Reductive opening of the benzylidene moieties in 7 and 8 gave access to the 4-hydroxy groups in 9 and 10. Ensuing fucosylation of 9 or galactosylation of 10 led to Lewis A (Le(a)) and Lewis X (Le(x)) trisaccharide building blocks 13 and 14, respectively. Their transformation into glycosyl donors 19 and 20 and subsequent reaction with 3b-O-unprotected lactose derivative 23 as acceptor furnished the Le(a)- and Le(x) pentasaccharide precursors 24 and 25. Exchange of the N-trichloroethoxycarbonyl group for an N-acetyl group and removal of the O-benzyl and O-acetyl protective groups afforded the desired Le(a)- and Lex-pentasaccharides 1 and 2.

  DOI：

  10.1080/07328309808002349