[(2R,3S,4R,5R,6S)-4-[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-methyl-3-phenylmethoxyoxan-2-yl]oxy-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-3-hydroxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl benzoate | 212713-56-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6S)-4-[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-methyl-3-phenylmethoxyoxan-2-yl]oxy-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-3-hydroxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl benzoate
• CAS: 212713-56-9
• 化学式: C₄₁H₅₆Cl₃NO₁₄Si
• 分子量: 921.338
• InChiKey: PIXIARAPVPXELR-LOKICZATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.63
• 重原子数：
  60
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  184
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6S)-4-[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-methyl-3-phenylmethoxyoxan-2-yl]oxy-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-3-hydroxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl benzoate 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 192.08h， 生成 C₄₇H₅₆Cl₃NO₂₃
  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 三氟甲磺酸三甲基硅酯 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.25h， 生成 [(2R,3S,4R,5R,6S)-4-[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-methyl-3-phenylmethoxyoxan-2-yl]oxy-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-3-hydroxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl benzoate
  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

文献信息

• Synthesis of the Sialyl Lewis X Epitope Attached to Glycolipids with Different Core Structures and their Selectin-Binding Characteristics in a Dynamic Test System
  作者：Christian Gege、Jan Vogel、Gerd Bendas、Ulrich Rothe、Richard R. Schmidt

  DOI：10.1002/(sici)1521-3765(20000103)6:1<111::aid-chem111>3.0.co;2-x

  日期：2000.1.3

  Sialyl Lewis X (sLe(X))/selectin-mediated leukocyte rolling along endothelial cells has recently gained wide interest. In this paper the influence of the spacer length of laterally clustered neoglycolipids 1a-d on cell rolling in a dynamic test system is investigated. The required di-O-hexadecyl glycerols with none, and with three, six, or nine ethylene glycol units as spacer groups (compounds 4a-d) could be readily obtained. The synthesis of 1-O-thexyldimethylsilyl-protected sLe(X) 24 was based on sialylation of 2,3,4-O-unprotected galactose derivative 11 with sialyl phosphite 8 as donor; this afforded the desired disaccharide 12, which was transformed into trichloroacetimidate 14 as disaccharide donor. Reaction of 3-O-unprotected glucosamine derivative 18 with fucosyl donor 20 afforded disaccharide 21, which was transformed into the 4-O-unprotected derivative 23. Reaction of 14 with 23 furnished the desired tetrasaccharide 24 in good yield. Transformation of 24 into the trichloroacetimidate 26 as donor, followed by the reaction with 4a-d as acceptor gave, after deprotection, the target molecules 1a-d. For comparison, 4d was also connected with a sialyl residue (-->31) and with an N-acetylglucosamine residue (-->34). Compounds 1c and 1d with a hexaethylene glycol and a nonaethylene glycol spacer, respectively, were much more efficient in mediating selectin-dependent cell rolling in the dynamic test system than compounds 1a and 1b, which had no spacer (1a), or only a triethylene glycol spacer (1b).