4-(D-allo/altro-pentit-1-yl)resorcinol | 284036-84-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(D-allo/altro-pentit-1-yl)resorcinol
• 英文别名: (2S,3R,4R)-1-(2,4-dihydroxyphenyl)pentane-1,2,3,4,5-pentol
• CAS: 284036-84-6
• 化学式: C₁₁H₁₆O₇
• 分子量: 260.244
• InChiKey: FMVJPYQUKMDOMH-UBJLHIIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  142
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-(D-allo/altro-pentit-1-yl)resorcinol 以 吡啶 为溶剂， 以85%的产率得到1,3-di-O-acetyl-4-(2,3,4,5-penta-O-acetyl-D-allo/altro-pentit-1-yl)resorcinol
  参考文献：
  名称：

  Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

  摘要：

  The reaction of sialyl phosphites 1, 22a-d, 28, 39, and 45 with acyl-protected riboside 5-phosphorous acids 2a,b and 23 directly furnished, without addition of a catalyst, under phosphite/phosphate exchange the corresponding beta-configured sialyl riboside monophosphates 3a,b, 24a-d, 29, 46, and 47. The synthesis of the starting materials, formation of the products, and their treatment with sodium methanolate in methanol and subsequent hydrolysis of the sialic acid ester moiety to provide the unprotected target molecules 4a,b, 25a-d, 30, 48, and 49 is described. Investigations with alpha(2-6)-sialyl-transferase from rat Liver showed that base replacement in CMP-Neu5Ac (4a,b) is not tolerated by the enzyme but that modifications of the 5-, 8-, or g-position of the neuraminic acid residue (25a-d, 30, 48, 49) are tolerated.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1467::aid-ejoc1467>3.0.co;2-e
• 作为产物：
  描述：

  2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose 在 10percent Pd/C 正丁基锂 、 barium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 50.25h， 生成 4-(D-allo/altro-pentit-1-yl)resorcinol
  参考文献：
  名称：

  Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

  摘要：

  The reaction of sialyl phosphites 1, 22a-d, 28, 39, and 45 with acyl-protected riboside 5-phosphorous acids 2a,b and 23 directly furnished, without addition of a catalyst, under phosphite/phosphate exchange the corresponding beta-configured sialyl riboside monophosphates 3a,b, 24a-d, 29, 46, and 47. The synthesis of the starting materials, formation of the products, and their treatment with sodium methanolate in methanol and subsequent hydrolysis of the sialic acid ester moiety to provide the unprotected target molecules 4a,b, 25a-d, 30, 48, and 49 is described. Investigations with alpha(2-6)-sialyl-transferase from rat Liver showed that base replacement in CMP-Neu5Ac (4a,b) is not tolerated by the enzyme but that modifications of the 5-, 8-, or g-position of the neuraminic acid residue (25a-d, 30, 48, 49) are tolerated.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1467::aid-ejoc1467>3.0.co;2-e

文献信息

• Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver
  作者：Gesche Dufner、Ralf Schwörer、Bernd Müller、Richard R. Schmidt

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1467::aid-ejoc1467>3.0.co;2-e

  日期：2000.4

  The reaction of sialyl phosphites 1, 22a-d, 28, 39, and 45 with acyl-protected riboside 5-phosphorous acids 2a,b and 23 directly furnished, without addition of a catalyst, under phosphite/phosphate exchange the corresponding beta-configured sialyl riboside monophosphates 3a,b, 24a-d, 29, 46, and 47. The synthesis of the starting materials, formation of the products, and their treatment with sodium methanolate in methanol and subsequent hydrolysis of the sialic acid ester moiety to provide the unprotected target molecules 4a,b, 25a-d, 30, 48, and 49 is described. Investigations with alpha(2-6)-sialyl-transferase from rat Liver showed that base replacement in CMP-Neu5Ac (4a,b) is not tolerated by the enzyme but that modifications of the 5-, 8-, or g-position of the neuraminic acid residue (25a-d, 30, 48, 49) are tolerated.