3-O-benzoyl-4,6-O-benzylidenyl-N-acetylgalactosamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 3-O-benzoyl-4,6-O-benzylidenyl-N-acetylgalactosamine
• 英文别名: [(2S,4aR,6S,7R,8R,8aR)-7-acetamido-6-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• 化学式: C₂₂H₂₃NO₇
• 分子量: 413.427
• InChiKey: GFPZIAKCJILCRW-BHNQRHOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三氯乙腈 、 3-O-benzoyl-4,6-O-benzylidenyl-N-acetylgalactosamine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 Benzoic acid (2S,4aR,6R,7R,8R,8aR)-7-acetylamino-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
  参考文献：
  名称：

  Steric Control of N-Acetylgalactosamine In Glycosidic Bond Formation

  摘要：

  N-Acetylgalactosamine, protected with a 4,6-cyclic acetal followed by selective acylation at 3-OH, provides an excellent donor for the synthesis of rx-glycosides, particularly the cancer associated antigens such as Tn, TF, Sialyl-Tn and Sialyl-TF. This fast and efficient synthesis is easily adaptable for commercial production of mucin type glycopeptides with O-linked carbohydrate structures which are currently being investigated as vaccines against cancers.

  DOI：

  10.1016/00404-0399(50)1442k-
• 作为产物：
  描述：

  苯甲酰氯 、 N-[(2S,4aR,6S,7R,8R,8aR)-6,8-dihydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide 以 吡啶 为溶剂， 生成 3-O-benzoyl-4,6-O-benzylidenyl-N-acetylgalactosamine
  参考文献：
  名称：

  Steric Control of N-Acetylgalactosamine In Glycosidic Bond Formation

  摘要：

  N-Acetylgalactosamine, protected with a 4,6-cyclic acetal followed by selective acylation at 3-OH, provides an excellent donor for the synthesis of rx-glycosides, particularly the cancer associated antigens such as Tn, TF, Sialyl-Tn and Sialyl-TF. This fast and efficient synthesis is easily adaptable for commercial production of mucin type glycopeptides with O-linked carbohydrate structures which are currently being investigated as vaccines against cancers.

  DOI：

  10.1016/00404-0399(50)1442k-

文献信息

• Steric Control of N-Acetylgalactosamine In Glycosidic Bond Formation
  作者：J Yule

  DOI：10.1016/00404-0399(50)1442k-

  日期：1995.9.18

  N-Acetylgalactosamine, protected with a 4,6-cyclic acetal followed by selective acylation at 3-OH, provides an excellent donor for the synthesis of rx-glycosides, particularly the cancer associated antigens such as Tn, TF, Sialyl-Tn and Sialyl-TF. This fast and efficient synthesis is easily adaptable for commercial production of mucin type glycopeptides with O-linked carbohydrate structures which are currently being investigated as vaccines against cancers.