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 | 172139-01-4

• 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: 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
• CAS: 172139-01-4
• 化学式: C₁₅H₁₉NO₆
• 分子量: 309.319
• InChiKey: OIXDAEIOQFFRMF-JNWWKETESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  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 在 吡啶 、 sodium hydroxide 、 三氟化硼乙醚 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 生成 (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-4-((2S,3R,4R,5R,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-amino-butyric acid
  参考文献：
  名称：

  A novel glycosyl donor for the synthesis of cancer specific core 5 and sialyl core 5 as glycopeptide building blocks

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(96)02490-2
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 、 苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 以85%的产率得到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
  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.
• 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.