5-o-羰基甲氧基-1,2-o-亚异丙基-3-o-对甲苯磺酰基-Alpha-D-呋喃木糖 | 74580-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-o-羰基甲氧基-1,2-o-亚异丙基-3-o-对甲苯磺酰基-Alpha-D-呋喃木糖
• 中文别名: 5-O-羰基甲氧基-1,2-O-亚异丙基-3-O-对甲苯磺酰基-Α-D-呋喃木糖
• 英文名称: 1,2-O-isopropylidene-5-O-(methoxycarbonyl)-3-O-tosyl-α-D-xylofuranose
• 英文别名: O¹,O²-isopropylidene-O⁵-methoxycarbonyl-O³-(toluene-4-sulfonyl)-α-D-xylofuranose；O¹,O²-Isopropyliden-O⁵-methoxycarbonyl-O³-(toluol-4-sulfonyl)-α-D-xylofuranose；5-O-Carbomethoxy-1,2-O-iso-propylidene-3-O-(P-tolyl-sulfonyl)-alpha-D-xylofuranose；[(3aR,5R,6S,6aR)-5-(methoxycarbonyloxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 4-methylbenzenesulfonate
• CAS: 74580-94-2
• 化学式: C₁₇H₂₂O₉S
• mdl: MFCD00015880
• 分子量: 402.422
• InChiKey: GWIBCLYQHGMNAQ-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.588
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-o-羰基甲氧基-1,2-o-亚异丙基-3-o-对甲苯磺酰基-Alpha-D-呋喃木糖 在 吡啶 、 甲醇 、 sodium 作用下， 反应 24.0h， 生成 O5-acetyl-O1,O2-isopropylidene-O3-(toluene-4-sulfonyl)-α-D-xylofuranose
  参考文献：
  名称：

  Nucleosides. 116. 1-(.beta.-D-Xylofuranosyl)-5-fluorocytosines with a leaving group on the 3' position. Potential double-barreled masked precursors of anticancer nucleosides

  摘要：

  Syntheses of five pairs of cytosine and 5-fluorocytosinexylofuranosyl nucleosides in which the 3'-hydroxyl group is replaced by Cl, Br, OMs, or OTs are described. Those xylosyl nucleosides with a good leaving group at the 3' position exhibit good inhibitory activity against L5178Y and P815 mouse leukemic cells in vitro at rather low concentrations, and like that of ara-C this cytotoxicity is reversed by 2'-deoxycytidine but not by thymidine. Xylosylcytosines are not active against ara-C resistant lines of L5178Y and P815 cells; however, the corresponding 5-fluorocytosine analogues exhibit significant cytotoxicity against these ara-C resistant leukemic cell lines, and this activity is reversed by thmidine but not by deoxycytidine. These data support the "double-barreled" masked precursor hypothesis in that xylosyl-5-fluorocytosines substituted at the 3' position by a good leaving group exhibit activity akin to that of ara-C in the ara-C sensitive lines, while these nucleosides act as 5-fluoropyrimidines in the ara-C resistant lines.

  DOI：

  10.1021/jm00184a006
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 氯仿 作用下， 生成 5-o-羰基甲氧基-1,2-o-亚异丙基-3-o-对甲苯磺酰基-Alpha-D-呋喃木糖
  参考文献：
  名称：

  Potential Anticancer Agents.¹ VII. Synthesis and Ammonolysis of Methyl 2,3-Anhydro-D-ribofuranoside

  摘要：

  DOI：

  10.1021/ja01552a057

文献信息

• Haworth et al., Recueil des Travaux Chimiques des Pays-Bas, 1938, vol. 57, p. 541,547
  作者：Haworth et al.

  DOI：——

  日期：——
• Nucleosides. 116. 1-(.beta.-D-Xylofuranosyl)-5-fluorocytosines with a leaving group on the 3' position. Potential double-barreled masked precursors of anticancer nucleosides
  作者：K. A. Watanabe、U. Reichman、C. K. Chu、D. H. Hollenberg、J. J. Fox

  DOI：10.1021/jm00184a006

  日期：1980.10

  Syntheses of five pairs of cytosine and 5-fluorocytosinexylofuranosyl nucleosides in which the 3'-hydroxyl group is replaced by Cl, Br, OMs, or OTs are described. Those xylosyl nucleosides with a good leaving group at the 3' position exhibit good inhibitory activity against L5178Y and P815 mouse leukemic cells in vitro at rather low concentrations, and like that of ara-C this cytotoxicity is reversed by 2'-deoxycytidine but not by thymidine. Xylosylcytosines are not active against ara-C resistant lines of L5178Y and P815 cells; however, the corresponding 5-fluorocytosine analogues exhibit significant cytotoxicity against these ara-C resistant leukemic cell lines, and this activity is reversed by thmidine but not by deoxycytidine. These data support the "double-barreled" masked precursor hypothesis in that xylosyl-5-fluorocytosines substituted at the 3' position by a good leaving group exhibit activity akin to that of ara-C in the ara-C sensitive lines, while these nucleosides act as 5-fluoropyrimidines in the ara-C resistant lines.
• Potential Anticancer Agents.¹ VII. Synthesis and Ammonolysis of Methyl 2,3-Anhydro-D-ribofuranoside
  作者：Charles D. Anderson、Leon Goodman、B. R. Baker

  DOI：10.1021/ja01552a057

  日期：1958.10