2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate | 263247-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate
• 英文别名: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-galactopyranosyl 2,2,2-trichloroacetimidate；Gal2Ac3Ac4Ac6Ac(b1-6)Gal2Ac3Ac4Ac(a)-O-C(NH)CCl3；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 263247-16-1
• 化学式: C₂₈H₃₆Cl₃NO₁₈
• 分子量: 780.949
• InChiKey: BQWSDTBLBHIXEF-PQYWDRMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate 、 dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到dodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-[2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)]-3,4-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a tetrasaccharide representing a minimal epitope of an arabinogalactan

  摘要：

  The hydrophobic alkyl chain-containing tetrasaccharide, dodecyl beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranosyl-(1-->6)-[alpha-L - arabinofuranosyl-(1-->2)]-beta-D-galactopyranoside, was synthesized efficiently using a convergent strategy. In coupling reactions, protected trichloroacetimidates proved to be better donors than their corresponding bromides in the preparation of the dodecyl disaccharide and trisaccharide. Zemplén deacylation provided the target tetramer in good overall yield.

  DOI：

  10.1016/s0008-6215(99)00252-9
• 作为产物：
  描述：

  双丙酮半乳糖 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苄胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of a tetrasaccharide representing a minimal epitope of an arabinogalactan

  摘要：

  The hydrophobic alkyl chain-containing tetrasaccharide, dodecyl beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranosyl-(1-->6)-[alpha-L - arabinofuranosyl-(1-->2)]-beta-D-galactopyranoside, was synthesized efficiently using a convergent strategy. In coupling reactions, protected trichloroacetimidates proved to be better donors than their corresponding bromides in the preparation of the dodecyl disaccharide and trisaccharide. Zemplén deacylation provided the target tetramer in good overall yield.

  DOI：

  10.1016/s0008-6215(99)00252-9

文献信息

• SYNTHESIS OF 3-<i>O</i>-ARABINOSYLATED (1→6)-β-<scp>D</scp>-GALACTAN EPITOPES
  作者：Qingfeng Pan、Yuguo Du、Fanzuo Kong*、Jingqi Pan、Mujian Lü

  DOI：10.1081/car-100104865

  日期：2001.4.30

  Two tetrameric arabinogalactans, β-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-(1→6)-[α-L-arabinofuranosyl-(1→3)]-D-galactopyranose (14) and α-L-arabinofuranosyl-(1→3)-β-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-(1→6)-D-galactopyranose (25), which are good candidates for CCRC-M7 epitope characterization, were synthesized efficiently using a convergent strategy. Migration of an acceptor acetyl

  两个四聚阿拉伯半乳聚糖，β- D-吡喃半乳糖-（1→6）-β- D-吡喃半乳糖-（1→6）-[α- L-阿拉伯呋喃糖基- （1→3）]- D-吡喃半乳糖（14）和α -L-阿拉伯呋喃糖基- （1→3）-β- D-吡喃半乳糖基-（1→6）-β- D-吡喃半乳糖基-（1→6）-D-吡喃半乳糖（25），它们是CCRC-M7的良好候选者抗原表位表征，使用收敛策略进行了有效合成。受体乙酰基的迁移被证明是合成的障碍，但是区域选择性糖基化或4- O受体的-苄基保护避免了这个问题，从而可以有效合成1→6连接的目标化合物。