di-O-acetyl-2-deoxy-L-fucopyranosyl bromide | 76248-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: di-O-acetyl-2-deoxy-L-fucopyranosyl bromide
• 英文别名: [(2S,3R,4S)-3-acetyloxy-6-bromo-2-methyloxan-4-yl] acetate
• CAS: 76248-11-8
• 化学式: C₁₀H₁₅BrO₅
• 分子量: 295.13
• InChiKey: DCYXHMVVTCMQQC-BOMAFOMESA-N

物化性质

• 沸点：
  315.0±42.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：

  di-O-acetyl-2-deoxy-L-fucopyranosyl bromide 在 2,4,6-三甲基吡啶 、 lithium hydroxide 、 silver trifluoromethanesulfonate 、 二甲基二环氧乙烷 作用下， 以 氯仿 、 水 、 苯 为溶剂， 反应 7.5h， 生成 (2S,3S,4S,6S)-6-((2S,3R,4R,6R)-6-Methoxy-2,4-dimethyl-4-nitro-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Synthetic Studies of the Cororubicin Oligosaccharide: Glycosylation of Branched Amino and Nitro Sugars

  摘要：

  Derivatives of the branched amino sugar methyl 3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-ribo-hexopyranoside and its 3-nitro analog were coupled with glycosyl donors of 3,4-di-O-acetyl-2,6-dideoxy-L-fucopyranose. Successful glycosylations were developed using the fucosyl bromide, activated with silver triflate, and the fucosyl oxysilane, activated with trimethylsilyl triflate. High stereoselectivities for the desired alpha-1,4 linkage were observed in both cases. The N-trifluoroacetamido disaccharide was deacylated and the amino group oxidized to nitro with dimethyldioxirane. An alternate route based on coupling of the fucosyl bromide with the nitro sugar methyl alpha-L-decilonitroside also gave the a-linked disaccharide, which is related to oligosaccharides found in the antibiotics cororubicin and arugomycin.

  DOI：

  10.1080/07328309808005767

文献信息

• Klaffke, Werner; Pudlo, Peter; Springer, Dirk, Liebigs Annalen der Chemie, 1991, # 6, p. 509 - 512
  作者：Klaffke, Werner、Pudlo, Peter、Springer, Dirk、Thiem, Joachim

  DOI：——

  日期：——
• Synthesis of 2'-deoxy-L-fucopyranosylcarminomycinone and -.epsilon.-pyrromycinone as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -.epsilon.-pyrromycinone
  作者：Hassan S. El Khadem、David L. Swartz

  DOI：10.1021/jm00133a023

  日期：1981.1

  Treatment of di-O-acetyl-2-deoxy-L-fucopyranosyl bromide with carminomycinone and epsilon-pyrromycinone in the presence of mercuric bromide and mercuric cyanide afforded 3',4'-diO-acetyl-2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone. Similarly, when di-O-acetyl-2-deoxy-D-erythrho-pentopyranosyl chloride was treated with daunomycinone, carminomycinone and epsilon-pyrromycinone, the di-O-acetyl derivatives of the anthracyclinone glycosides were obtained. Deacetylation of the previous acetates with sodium methoxide afforded 2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone, as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -epsilon-pyrromycinone. 2'-Deoxy-L-fucopyranosylcarminomycinone was found to be more active than carminomycin at higher dosages on L1210.