3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl chloride | 64605-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl chloride
• 英文别名: [(2S,3R,4S,6S)-3-acetyloxy-6-chloro-2-methyloxan-4-yl] acetate
• CAS: 64605-19-2
• 化学式: C₁₀H₁₅ClO₅
• 分子量: 250.679
• InChiKey: QXXHXMJEBAQRTO-UKIQFFJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl chloride 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 四丁基碘化铵 、 二正丁基氧化锡 、 三乙胺 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 71.0h， 生成 methyl 4-O-(4-O-(4-O-acetyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  Shelton, Cathryn J.; Harding, Margaret M., Journal of Chemical Research, Miniprint, 1995, # 5, p. 1201 - 1219

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 在 盐酸 作用下， 以 苯 为溶剂， 反应 0.25h， 生成 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl chloride
  参考文献：
  名称：

  A Practical Method for the Stereoselective Generation of β-2-Deoxy Glycosyl Phosphates

  摘要：

  beta-2-Deoxy sugar nucleotides are substrates used by a variety of glycosyltransferases (Gtfs). We have developed a chemical route to synthesize beta-2-deoxy sugar phosphates that starts from a-glycosyl chlorides. Our approach reliably provides access to a range of NDP beta-2-deoxy sugars essential for studying glycosyltransferases involved in the synthesis of biologically active natural products.

  DOI：

  10.1021/ol049187f

文献信息

• Aminonaphthacene derivatives
  申请人：Sumitomo Pharmaceuticals Company

  公开号：US04673668A1

  公开（公告）日：1987-06-16

  9-Aminonaphthacene derivative having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are both hydrogen atoms or either one of them is a hydrogen atom and the other is hydroxy group or methoxy group; R.sup.3 is acetyl group or 1-hydroxyethyl group; R.sup.4 is a hydrogen atom; R.sup.5 is a hydrogen atom, hydroxy group, lower alkanoyloxy group, amino group, halogen-substituted lower alkanoylamino group or morpholino group; R.sup.6 is a hydrogen atom, hydroxy group, lower alkanoyloxy group or tetrahydropyranyloxy group; R.sup.7 is a hydrogen atom or methyl group; R is a hydrogen atom; and n is zero or one, which is useful as anti-cancer chemical agents with lower toxicity and with little local irritation and is able to orally be applied.

  具有以下式子的9-氨基萘啶衍生物：##STR1## 其中R.sup.1和R.sup.2都是氢原子，或者其中一个是氢原子，另一个是羟基或甲氧基；R.sup.3是乙酰基或1-羟乙基基团；R.sup.4是氢原子；R.sup.5是氢原子、羟基、较低的烷酰氧基团、氨基、卤代较低的烷酰胺基团或吗啡环基团；R.sup.6是氢原子、羟基、较低的烷酰氧基团或四氢吡喃氧基团；R.sup.7是氢原子或甲基基团；R是氢原子；n为零或一。该化合物是一种抗癌化学药剂，具有较低的毒性和较少的局部刺激，并且可以口服应用。
• 7-O-(2,6-Dideoxy-.alpha.-L-lyxo-hexopyranosyl)-daunomycinone, desmethoxy
  申请人：The United States of America as represented by the Department of Health,

  公开号：US04201773A1

  公开（公告）日：1980-05-06

  A series of compounds showing high antileukemic activity against P388 murine leukemia and increased aqueous solubility due to substitution of --OH for the known --NH.sub.2 at the 3' position of the hexopyranose sugar, i.e., daunosamine. These compounds are coupled products of aglycon selected from daunomycinone, desmethoxy daunomycinone, adriamycinone and carminomycinone. These compounds are coupled at the 0-7 position of the aglycon with an .alpha.-L-lyxo hexopyranose sugar, which sugar isomer particularly sustains or potentiates the biological activity of the coupled compound as well as ameliorates the dose related cardiotoxicity of the parent and known compounds set out below: ##STR1##

  一系列化合物表现出高抗白血病活性，对P388小鼠白血病具有高度抑制作用，并由于在己糖糖的3'位置上的已知的--NH.sub.2被--OH取代而具有增加的水溶性，即daunosamine。这些化合物是选自daunomycinone、desmethoxy daunomycinone、adriamycinone和carminomycinone的无糖苷酮的偶联产物。这些化合物在无糖苷酮的0-7位置与.alpha.-L-lyxo己糖糖偶联，这种糖异构体特别维持或增强了偶联化合物的生物活性，并改善了以下父化合物和已知化合物的剂量相关心脏毒性：##STR1##
• Dufat-Trinh, Hahn van; Seguin, Elisabeth; Tillequin, Francois, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 12, p. 3294 - 3300
  作者：Dufat-Trinh, Hahn van、Seguin, Elisabeth、Tillequin, Francois、Monneret, Claude、Koch, Michel

  DOI：——

  日期：——
• Synthesis and antitumor activity of 7-O-(3,4-di-O-acetyl-2,6-dideoxy-α-l-lyxo-hexopyranosyl)adriamycinone
  作者：Derek Horton、Waldemar Priebe、Willam R. Turner

  DOI：10.1016/s0008-6215(00)85592-5

  日期：1981.7

  The title compound (7), the 3'-acetoxy-4'-O-acetyl analog of adriamycin (doxorubicin), was synthesized in approximately 50% net yield from daunomycinone by bromination at C-14, glycosylation of the product at O-7 with 3,4-di-O-acetyl-2,6-dideoxy-alpha-L-lyxo-hexopyranosyl chloride, and replacement of the 14-bromo substituent by a hydroxyl group; other possible routes to 7 gave lower yields. The product 7, a non-aminated analog of the anthracycline antibiotics, showed high antitumor activity coupled with low acute toxicity in a broad range of tests in mice.
• Synthesis of 7-[3-amino-2,3,6-trideoxy-4-O-(2,6-dideoxy-α-l-lyxo-hexopyranosyl)-α-l-lyxo-hexopyranosyl] daunomycinone
  作者：Hassan S. El Khadem、Daisaburo Matsuura

  DOI：10.1016/s0008-6215(00)80810-1

  日期：1982.2