O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-(2-azido-6-O-benzyl-2-deoxy-α/β-D-glucopyranosyl) trichloroacetimidate | 188656-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-(2-azido-6-O-benzyl-2-deoxy-α/β-D-glucopyranosyl) trichloroacetimidate
• 英文别名: [(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3S,4R,5R)-5-azido-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 188656-44-2
• 化学式: C₆₁H₆₇Cl₃N₄O₁₇
• 分子量: 1234.58
• InChiKey: UHEGLMDVVDPWDP-WAFPKVDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  85
• 可旋转键数：
  30
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  219
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  benzyl O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 、 O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-(2-azido-6-O-benzyl-2-deoxy-α/β-D-glucopyranosyl) trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以75%的产率得到
  参考文献：
  名称：

  Hummel; Schmidt, Polish Journal of Chemistry, 1999, vol. 73, # 6, p. 941 - 954

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-butyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 NaCNBH₃*HCl 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 为溶剂， 生成 O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-(2-azido-6-O-benzyl-2-deoxy-α/β-D-glucopyranosyl) trichloroacetimidate
  参考文献：
  名称：

  A versatile synthesis of the lactoneo-series antigens — synthesis of sialyl dimer Lewis X and of dimer Lewis Y

  摘要：

  Readily available fucosyl alpha(1-3)azidoglucose disaccharide 6 is transformed with galactosyl donors 7 and 8 into Lewis X trisaccharide building blocks 9 and 12, respectively, in high yield. Their suitability for the construction of the lactoneo-series glycosphingolipids is demonstrated For instance, 9 readily affords glycosyl donor 10 and acceptor 11, which permits the required regioselective 3-O-sialylation of the galactose moiety; Thus, from 11 and 12 hexasaccharide 14 is generated which afforded with lactose acceptor 17 the decisive octasaccharide intermediate 18 which is then transformed either into sialyl dimer Lewis X (1) or into dimeric Lewis Y (2). (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00006-3

文献信息

• Hummel; Schmidt, Polish Journal of Chemistry, 1999, vol. 73, # 6, p. 941 - 954
  作者：Hummel、Schmidt

  DOI：——

  日期：——
• A versatile synthesis of the lactoneo-series antigens — synthesis of sialyl dimer Lewis X and of dimer Lewis Y
  作者：Gerd Hummel、Richard R Schmidt

  DOI：10.1016/s0040-4039(97)00006-3

  日期：1997.2

  Readily available fucosyl alpha(1-3)azidoglucose disaccharide 6 is transformed with galactosyl donors 7 and 8 into Lewis X trisaccharide building blocks 9 and 12, respectively, in high yield. Their suitability for the construction of the lactoneo-series glycosphingolipids is demonstrated For instance, 9 readily affords glycosyl donor 10 and acceptor 11, which permits the required regioselective 3-O-sialylation of the galactose moiety; Thus, from 11 and 12 hexasaccharide 14 is generated which afforded with lactose acceptor 17 the decisive octasaccharide intermediate 18 which is then transformed either into sialyl dimer Lewis X (1) or into dimeric Lewis Y (2). (C) 1997, Elsevier Science Ltd.