2-azidoethyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 503159-51-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 503159-51-1
• 化学式: C₇₂H₈₀N₄O₁₇
• 分子量: 1273.44
• InChiKey: IOQUIVYZNJFBGM-AQCVGOOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.02
• 重原子数：
  93.0
• 可旋转键数：
  31.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  236.54
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-2,6-di-O-benzoyl-3-O-chloroacetyl-β-D-galactopyranosyl bromide 、 2-azidoethyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以690 mg的产率得到2-azidoethyl 4-O-acetyl-2,6-di-O-benzoyl-3-O-chloroacetyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-...
  参考文献：
  名称：

  Synthesis of a spacer-armed disulfated tetrasaccharide of SB1a, a carbohydrate hapten associated with human hepatocellular carcinoma

  摘要：

  A disulfated tetrasaccharide fragment with a spacer arm of human hepatocellular carcinoma carbohydrate antigen SB1a, namely, 2-aminoethyl 3-O-sulfo-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-galactopyranosyl-(1 --> 4)-3-O-sulfo-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranoside was synthesized via a [2 + 1 + 1] block building mode. In the last coupling step toward the trisaccharide acceptor 8, benzoyl protected galactosyl bromide donor 14 was found to be much more reactive than the acetyl-protected donors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00291-4
• 作为产物：
  描述：

  2-azidoethyl 2-amino-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 吡啶 、 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 38.0h， 生成 2-azidoethyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a spacer-armed disulfated tetrasaccharide of SB1a, a carbohydrate hapten associated with human hepatocellular carcinoma

  摘要：

  A disulfated tetrasaccharide fragment with a spacer arm of human hepatocellular carcinoma carbohydrate antigen SB1a, namely, 2-aminoethyl 3-O-sulfo-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-galactopyranosyl-(1 --> 4)-3-O-sulfo-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranoside was synthesized via a [2 + 1 + 1] block building mode. In the last coupling step toward the trisaccharide acceptor 8, benzoyl protected galactosyl bromide donor 14 was found to be much more reactive than the acetyl-protected donors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00291-4