Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester | 212713-54-7

• 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-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2S,3R,4R,5S,6S)-4-acetyloxy-6-[(2S,3R,4R,5S,6R)-2-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-5-hydroxy-6-(phenylmethoxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl]oxy-2-methyl-5-phenylmethoxyoxan-3-yl] acetate
• CAS: 212713-54-7
• 化学式: C₄₁H₅₈Cl₃NO₁₃Si
• 分子量: 907.355
• InChiKey: YKIXSSWDHAESQF-XIBDHQHTSA-N

物化性质

• 沸点：
  827.408±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.285±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  167
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester 在 三氟化硼乙醚 、 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 为溶剂， 反应 192.25h， 生成 Bn(-2)Fuc3Ac4Ac(a1-3)[Gal2Ac3Ac4Ac6Ac(b1-4)][TrocNH(-2d)][Bn(-6)]Glc(b)-O-C(NH)CCl3
  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：

  苯甲醛二甲缩醛 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.08h， 生成 Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(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