thexyldimethylsilyl O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside | 212713-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thexyldimethylsilyl O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S,3R,4R,5S,6R)-5-[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-methyl-3-phenylmethoxyoxan-2-yl]oxy-2-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-6-(phenylmethoxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 212713-57-0
• 化学式: C₅₅H₇₆Cl₃NO₂₂Si
• 分子量: 1237.65
• InChiKey: VVECTXZQRSFMCI-BZSHWOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  82
• 可旋转键数：
  31
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  270
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  thexyldimethylsilyl O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 192.0h， 以93%的产率得到Gal2Ac3Ac4Ac6Ac(b1-3)[Bn(-2)Fuc3Ac4Ac(a1-4)][TrocNH(-2d)][Bn(-6)]b-Glc
  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：

  2,2,2-trichloroethyl N-[(4aR,6S,7R,8R,8aS)-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]carbamate 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 thexyldimethylsilyl O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
  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