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 | 171973-77-6

• 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: 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
• 英文别名: [(2S,4aR,6R,7R,8R,8aR)-7-acetamido-2-phenyl-6-(2,2,2-trichloroethanimidoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• CAS: 171973-77-6
• 化学式: C₂₄H₂₃Cl₃N₂O₇
• 分子量: 557.815
• InChiKey: KXEHVNPBAPICIP-AMLBEPSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(9-芴甲氧羰基)-L-丝氨酸苯甲酰甲酯 、 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 在 calcium sulfate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 生成 Benzoic acid (2S,4aR,6S,7R,8R,8aR)-7-acetylamino-6-[(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(2-oxo-2-phenyl-ethoxycarbonyl)-ethoxy]-2-phenyl-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：

  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-

文献信息

• A novel glycosyl donor for the synthesis of cancer specific core 5 and sialyl core 5 as glycopeptide building blocks
  作者：Dongxu Qiu、R.Rao Koganty

  DOI：10.1016/s0040-4039(96)02490-2

  日期：1997.2

  Trichloroacetimidate at 1 and 3 position of 4,6-benzylidenyl N-acetylgalactosamine serves as a leaving group for glycosylation and a selective and acid sensitive protecting group respectively. This versatile donor, while forming exclusive alpha-glycoside with serine/threonine, serves as a fascile precursor to 3-OH which can be generated in acid medium without affecting 4,6-acetal protecting group or the protecting groups of serine/threonine. Synthesis of cancer associated carbohydrate Core 5 and its sialylated analog are accomplished through the use of this donor. (C) 1997, Elsevier Science Ltd.
• 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.